Welcome to LookChem.com Sign In|Join Free

CAS

  • or

41138-61-8

Post Buying Request

41138-61-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

41138-61-8 Usage

Description

METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE is a complex organic compound with a specific stereochemistry and functional groups. It is characterized by its molecular structure, which includes a cyclopentene ring, a hydroxyl group, and a ketone group. METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE is of interest in various fields due to its unique properties and potential applications.

Uses

1. Pharmaceutical Industry:
METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE is used as an active pharmaceutical ingredient (API) for the development of drugs targeting specific medical conditions. Its unique structure and functional groups allow for the modulation of biological pathways and interactions with target molecules, making it a promising candidate for therapeutic applications.
2. Synthesis of Other Compounds:
In the field of organic chemistry, METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE can be used as a key intermediate in the synthesis of other complex organic molecules. Its functional groups can be further modified or used as a starting point for the creation of novel compounds with specific properties and applications.
3. Research and Development:
METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE is also used in research and development settings to study its properties, reactivity, and potential applications in various fields. This includes exploring its use in drug discovery, material science, and other areas where novel organic compounds are of interest.
4. Misoprostol Development:
METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE is used as a key component in the development of misoprostol, a medication used for the treatment of peptic ulcer disease. Misoprostol is an ingredient of (+)-norprostol, and its synthesis involves the use of METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE as a starting material or intermediate.

Synthesis Reference(s)

Synthesis, p. 781, 1986 DOI: 10.1055/s-1986-31779

Check Digit Verification of cas no

The CAS Registry Mumber 41138-61-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,1,3 and 8 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 41138-61:
(7*4)+(6*1)+(5*1)+(4*3)+(3*8)+(2*6)+(1*1)=88
88 % 10 = 8
So 41138-61-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H20O4/c1-17-13(16)7-5-3-2-4-6-10-8-11(14)9-12(10)15/h8,11,14H,2-7,9H2,1H3/t11-/m0/s1

41138-61-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Aldrich

  • (463981)  Methyl(R)-(+)-3-hydroxy-5-oxo-1-cyclopentene-1-heptanoate  97%

  • 41138-61-8

  • 463981-100MG

  • 1,267.11CNY

  • Detail

41138-61-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE

1.2 Other means of identification

Product number -
Other names Methyl (R)-(+)-3-hydroxy-5-oxo-1-cyclopentene-1-heptanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:41138-61-8 SDS

41138-61-8Synthetic route

methyl 7-<3(R)-(acetyloxy)-5-oxo-1-cyclopenten-1-yl>heptanoate
127126-27-6

methyl 7-<3(R)-(acetyloxy)-5-oxo-1-cyclopenten-1-yl>heptanoate

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
With guanidine nitrate98%
With guanidine nitrate In methanol at 0℃;
7-{5-oxo-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopent-1-en-1-yl}heptanoic acid methyl ester
60934-42-1

7-{5-oxo-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopent-1-en-1-yl}heptanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water for 24h; Ambient temperature;88%
Benzoic acid (R)-4-hydroxy-2-(6-methoxycarbonyl-hexyl)-3-oxo-cyclopent-1-enyl ester
41138-65-2

Benzoic acid (R)-4-hydroxy-2-(6-methoxycarbonyl-hexyl)-3-oxo-cyclopent-1-enyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
(i) Al, (ii) AcOH; Multistep reaction;
7-((R)-4-Hydroxy-2-isopropoxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester
53147-05-0

7-((R)-4-Hydroxy-2-isopropoxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
(i) Al, (ii) AcOH; Multistep reaction;
7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
41138-69-6

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran
7-[(R)-3-Oxo-5-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-heptanoic acid methyl ester

7-[(R)-3-Oxo-5-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-heptanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
With acetic acid
7-((S)-3-Methanesulfonyloxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester
251659-67-3

7-((S)-3-Methanesulfonyloxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
With guanidine nitrate In methanol at 0℃; for 0.25h; Substitution; Mitsunobu inversion;
8-(furan-2-yl)-8-oxooctanoic acid methyl ester
38199-47-2

8-(furan-2-yl)-8-oxooctanoic acid methyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating
2: 46 percent / PPL
3: 98 percent / guanidine
View Scheme
suberic acid monomethyl ester
3946-32-5

suberic acid monomethyl ester

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating
2: 46 percent / PPL
3: 98 percent / guanidine
View Scheme
methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate
40098-26-8

methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / PPL
2: 98 percent / guanidine
View Scheme
Multi-step reaction with 2 steps
1: lipase (PPL)
2: quanidine / methanol / 0 °C
View Scheme
methyl 7-(2-hydroxy-5-oxocyclopent-3-enyl)heptanoate
98818-31-6

methyl 7-(2-hydroxy-5-oxocyclopent-3-enyl)heptanoate

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating
2: 46 percent / PPL
3: 98 percent / guanidine
View Scheme
methyl 8-(2-furyl)-8-hydroxy-octanoate
101650-79-7

methyl 8-(2-furyl)-8-hydroxy-octanoate

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating
2: 46 percent / PPL
3: 98 percent / guanidine
View Scheme
methyl 7-<3(S)-(hydroxy)-5-oxo-1-cyclopenten-1-yl>heptanoate
42038-75-5

methyl 7-<3(S)-(hydroxy)-5-oxo-1-cyclopenten-1-yl>heptanoate

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / -10 °C
2: guanidine / methanol / 0.25 h / 0 °C
View Scheme
C7H13IO2Zn
131392-85-3

C7H13IO2Zn

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) CuCN / 2) THF, -78 deg C up to r.t.
2: n-Bu4NF / tetrahydrofuran
View Scheme
(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone
117254-03-2

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) CuCN / 2) THF, -78 deg C up to r.t.
2: n-Bu4NF / tetrahydrofuran
View Scheme
2-(6-Methoxycarbonylhexyl)-cyclopentan-1,3,4-trion
41138-63-0

2-(6-Methoxycarbonylhexyl)-cyclopentan-1,3,4-trion

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (microbiological transformation)
2: Et3N
3: (i) Al, (ii) AcOH
View Scheme
Multi-step reaction with 3 steps
1: (microbiological transformation)
2: K2CO3
3: (i) Al, (ii) AcOH
View Scheme
2-(6'-carbomethoxyhexyl)-4(R)-hydroxy-cyclopentane-1,3-dione
41138-64-1

2-(6'-carbomethoxyhexyl)-4(R)-hydroxy-cyclopentane-1,3-dione

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N
2: (i) Al, (ii) AcOH
View Scheme
Multi-step reaction with 2 steps
1: K2CO3
2: (i) Al, (ii) AcOH
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
41138-69-6

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide98%
With 1H-imidazole In N,N-dimethyl-formamide for 0.5h; Ambient temperature;95%
With 1H-imidazole; triethylamine In N,N-dimethyl-formamide84%
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
41138-69-6

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at -78 - 20℃; for 15h; silylation;89%
With 2,6-dimethylpyridine In dichloromethane at -78 - 20℃; for 15.5h;
triethylsilyl chloride
994-30-9

triethylsilyl chloride

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

methyl-7-[5-oxo-3(R)-[(triethylsilyl)oxy]-1-cyclopenten-1yl]-heptanoate
118456-54-5

methyl-7-[5-oxo-3(R)-[(triethylsilyl)oxy]-1-cyclopenten-1yl]-heptanoate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; Etherification;88%
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

(-)-1-mercapto-2(S)-heptanol
82542-28-7

(-)-1-mercapto-2(S)-heptanol

A

5-(6-methoxycarbonylhexyl)-3-<2(S)-hydroxyheptylthio>-2-cyclopentenone
82542-34-5

5-(6-methoxycarbonylhexyl)-3-<2(S)-hydroxyheptylthio>-2-cyclopentenone

B

13,14-dihydro-13-thia-prostaglandin-E1 methylester
82542-32-3

13,14-dihydro-13-thia-prostaglandin-E1 methylester

C

/PBNDC003-1180/

/PBNDC003-1180/

Conditions
ConditionsYield
With triethylamine In methanol for 48h; Ambient temperature;A 7.9%
B 12.3%
C n/a
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

n-hexylmagnesium bromide
3761-92-0

n-hexylmagnesium bromide

(-)-methyl 7-[(1S,2R)-2-hexyl-5-oxocyclopent-3-enyl]heptanoate
947409-07-6

(-)-methyl 7-[(1S,2R)-2-hexyl-5-oxocyclopent-3-enyl]heptanoate

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0 - 30℃; for 36h;
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

(-)-methyl 7-[(1S,2R,5R)-2-hexyl-5-hydroxycyclopentyl]heptanoate

(-)-methyl 7-[(1S,2R,5R)-2-hexyl-5-hydroxycyclopentyl]heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; diethyl ether / 36 h / 0 - 30 °C
2: L-selectride / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / -78 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

methyl 7-(5-but-3-enyl-2-hydroxy-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate
221629-33-0

methyl 7-(5-but-3-enyl-2-hydroxy-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-[(1R,2R,3R,5S)-2-But-3-enyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-heptanoic acid methyl ester
221629-43-2

7-[(1R,2R,3R,5S)-2-But-3-enyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-heptanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate
221629-44-3

methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiazol-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid methyl ester
1027145-33-0

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiazol-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: triethylamine / benzene / 20 h / 0 - 20 °C
6.1: HF/pyridine / acetonitrile / 3 h / 0 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiophen-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid methyl ester

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiophen-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: triethylamine / benzene / 20 h / 0 - 20 °C
6.1: HF/pyridine / acetonitrile / 3 h / 0 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylsulfanyl-butyl)-cyclopentyl]-heptanoic acid methyl ester
221629-35-2

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylsulfanyl-butyl)-cyclopentyl]-heptanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: triethylamine / benzene / 20 h / 0 - 20 °C
6.1: HF/pyridine / acetonitrile / 3 h / 0 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiophen-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid

7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiophen-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: triethylamine / benzene / 20 h / 0 - 20 °C
6.1: HF/pyridine / acetonitrile / 3 h / 0 °C
7.1: LiOH / tetrahydrofuran; H2O / 20 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylamino-butyl)-cyclopentyl]-heptanoic acid

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylamino-butyl)-cyclopentyl]-heptanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: magnesium perchlorate / tetrahydrofuran / 3 h / Heating
6.1: HF/pyridine / acetonitrile / 5 h / 0 °C
7.1: 57 percent / LiOH / tetrahydrofuran; H2O / 20 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylamino-butyl)-cyclopentyl]-heptanoic acid methyl ester
221629-38-5

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylamino-butyl)-cyclopentyl]-heptanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: magnesium perchlorate / tetrahydrofuran / 3 h / Heating
6.1: HF/pyridine / acetonitrile / 5 h / 0 °C
View Scheme
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
41138-61-8

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylsulfanyl-butyl)-cyclopentyl]-heptanoic acid

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylsulfanyl-butyl)-cyclopentyl]-heptanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C
2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating
2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C
3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C
4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C
5.1: triethylamine / benzene / 20 h / 0 - 20 °C
6.1: HF/pyridine / acetonitrile / 3 h / 0 °C
7.1: LiOH / tetrahydrofuran; H2O / 20 °C
View Scheme

41138-61-8Relevant articles and documents

An efficient synthesis of enantiomerically pure (1R,2S,5S)- and (1S,2R,5R)-rosaprostol methyl esters

Murcia, M. Carmen,De La Herran, Gabriela,Plumet, Joaquín,Csaky, Aurelio G.

, p. 1553 - 1556 (2008/02/05)

We report a concise synthesis of the enantiomerically pure 1,2-trans-1,5-cis-methyl esters of rosaprostol, a prostaglandin derivative used for the treatment of gastric and duodenal ulcers, using as key step the chemo- and stereoselective Michael addition of a Grignard reagent to an unprotected hydroxycyclopentenone. Georg Thieme Verlag Stuttgart.

An efficient asymmetric synthesis of prostaglandin E1

Rodriguez, Ana,Nomen, Miguel,Spur, Bernd Werner,Godfroid, Jean-Jacques

, p. 2655 - 2662 (2007/10/03)

An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE1 5 in high yield.

Production of cyclopentenones

-

, (2008/06/13)

A process for preparing an optically active cyclopentenone of the formula: wherein R is a hydrogen atom or a lower alkyl group and n is an integer of 4 to 8, which comprises contacting a dl-cyclo-pentenone ester of the formula: wherein R and n are each as defined above and R′ is a lower alkyl group optionally substituted with halogen on an enzyme having a capability of hydrolyzing selectively either one of the d- or l-form isomer in the dl-cyclopentenone ester (II) in an aqueous medium for asymmetric hydrolysis.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 41138-61-8