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3,5-Di-o-(p-toluyl)-2-deoxy-d-ribofuranosyl chloride

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Name

3,5-Di-o-(p-toluyl)-2-deoxy-d-ribofuranosyl chloride

EINECS 224-367-3
CAS No. 4330-21-6 Density 1.28 g/cm3
PSA 27.69000 LogP 4.48360
Solubility N/A Melting Point 117-119 °C
Formula C21H21ClO5 Boiling Point 518.414 °C at 760 mmHg
Molecular Weight 388.848 Flash Point 185.58 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 4330-21-6 (2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)) Hazard Symbols IrritantXi
Synonyms

D-erythro-Pentofuranosylchloride, 2-deoxy-, di-p-toluate, α- (8CI);p-Toluic acid, diester with2-deoxy-α-D-erythro-pentofuranosylchloride (8CI);1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose;2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride;Hoffer's α-chlorosugar;NSC 148837;

Article Data 30

3,5-Di-o-(p-toluyl)-2-deoxy-d-ribofuranosyl chloride Synthetic route

4330-34-1

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
With acetyl chloride In acetic acid at 20℃;79%
With hydrogenchloride In acetic acid at 10℃; for 1h;72%
With hydrogenchloride; acetic acid In 1,4-dioxane70%
78185-64-5

1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0℃; for 0.166667h;72%
874-60-2

4-methyl-benzoyl chloride

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Stage #1: D-2-deoxyribose With acetyl chloride In methanol at 20℃; for 1.16667h; Inert atmosphere;
Stage #2: 4-methyl-benzoyl chloride With pyridine In methanol at 0 - 20℃; Inert atmosphere;
Stage #3: With acetic acid; acetyl chloride In methanol at 0℃; Inert atmosphere;
36%
78185-65-6

1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranose

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
With hydrogenchloride; acetic acid
4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: AcCl / 2 h / 20 °C
1.2: DMAP; pyridine / 12 h / 0 °C
2.1: 72 percent / HCl gas / diethyl ether / 0.17 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 96 percent / hydrogen chloride / 2 h
2: 85 percent / pyridine / 20 °C
3: 72 percent / HCl / acetic acid / 1 h / 10 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / 0.42 h / 20 °C
2: pyridine / 0 - 20 °C / Inert atmosphere
3: hydrogenchloride; acetic acid
View Scheme
874-60-2

4-methyl-benzoyl chloride

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: AcCl / 2 h / 20 °C
1.2: DMAP; pyridine / 12 h / 0 °C
2.1: 72 percent / HCl gas / diethyl ether / 0.17 h / 0 °C
View Scheme
13222-85-0

p-methylbenzoic anhydride

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / NaH / tetrahydrofuran / 4 h / 60 - 70 °C
2: HCl / diethyl ether
View Scheme
874-60-2

4-methyl-benzoyl chloride

resin-bound 4-methylbenzylamine

resin-bound 4-methylbenzylamine

4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / Et3N / acetone
2: HCl / diethyl ether
View Scheme
Multi-step reaction with 3 steps
1: Et3N; H2O / acetone / 2 h
2: 90 percent / NaH / tetrahydrofuran / 4 h / 60 - 70 °C
3: HCl / diethyl ether
View Scheme
4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / Et3N / acetone
2: HCl / diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / pyridine / 20 °C
2: 72 percent / HCl / acetic acid / 1 h / 10 °C
View Scheme
Multi-step reaction with 2 steps
1: pyridine / Ambient temperature
2: HCl
View Scheme
4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HCl / 0.42 h / Ambient temperature
2: pyridine / Ambient temperature
3: HCl
View Scheme

3,5-Di-o-(p-toluyl)-2-deoxy-d-ribofuranosyl chloride Specification

The α-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-methylbenzoate), with the CAS registry number 4330-21-6, is also known as 2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl chloride. It belongs to the product categories of Carbohydrates; Carbohydrates A to; Carbohydrates D-F Biochemicals and Reagents; Monosaccharide. Its EINECS registry number is 224-367-3. This chemical's molecular formula is C21H21ClO5 and molecular weight is 388.84. What's more, its IUPAC name is called [(2R,3S,5R)-5-Chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate.

Physical properties about α-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-methylbenzoate) are: (1)ACD/LogP: 5.23; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.23; (4)ACD/LogD (pH 7.4): 5.23; (5)ACD/BCF (pH 5.5): 5523.34; (6)ACD/BCF (pH 7.4): 5523.34; (7)ACD/KOC (pH 5.5): 16605.81; (8)ACD/KOC (pH 7.4): 16605.81; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 61.83 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 101.3 cm3; (15)Molar Volume: 302.9 cm3; (16)Surface Tension: 50.8 dyne/cm; (17)Density: 1.28 g/cm3; (18)Flash Point: 185.6 °C; (19)Enthalpy of Vaporization: 79.09 kJ/mol; (20)Boiling Point: 518.4 °C at 760 mmHg; (21)Vapour Pressure: 7.5E-11 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O[C@@H]1[C@H](O[C@H](Cl)C1)COC(=O)c2ccc(cc2)C)c3ccc(cc3)C
(2) InChI: InChI=1/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19-/m0/s1
(3) InChIKey: FJHSYOMVMMNQJQ-OTWHNJEPBB

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