1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid

Base Information

• Chemical Name: 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid
• CAS No.: 910811-37-9
• Molecular Formula: C₂₇H₃₅NO₄S
• Molecular Weight: 469.645
• Mol file: 910811-37-9.mol

Synonyms:1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid

Chemical Property of 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid

There total 14 articles about 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 35.0%

glycolic Acid (79-14-1) + 3-(4-(3-aminopropoxy)-3,5-dimethylphenyl)-1-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propan-1-one (910812-29-2) → 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid (910811-37-9)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm4014373

Reference yield:

glycolic Acid (79-14-1) + 3-[4-(3-amino-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethy)-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one → 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid (910811-37-9)

Guidance literature:

With DIPEA; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;

Reference yield:

(+)-Δ3-carene (498-15-7,19079-29-9) → 1-(3-(2,6-dimethyl-4-(3-oxo-3-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propyl)phenoxy)propyl)azetidine-3-carboxylic acid (910811-37-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: ozone / methanol / -65 °C

1.2: 2 h / 20 - 35 °C

2.1: thionyl chloride / 0.5 h / 0 °C

3.1: sodium methylate / methanol / 1 h / Reflux

4.1: triphenylphosphine; tetrachloromethane / tetrachloromethane / 65 °C

5.1: sodium ethanolate / ethanol / 0.08 h / 20 °C

5.2: 1 h / 20 °C

5.3: 1 h / 75 °C

6.1: lithium hydroxide; water / ethanol / 2 h / 75 °C

7.1: diethyl ether / 35 °C

8.1: hydrogenchloride / ethanol; isopropyl alcohol / 20 h / 20 °C

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 3 h / 20 °C / 1125.11 Torr

10.1: sodium hydroxide / water; isopropyl alcohol / 5 h / 70 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

12.1: ammonia / methanol / 22 h / 70 °C / Sealed tube

13.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 20 °C

With hydrogenchloride; tetrachloromethane; thionyl chloride; palladium 10% on activated carbon; ammonia; water; hydrogen; sodium methylate; sodium ethanolate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; 3.1: |Dieckmann Condensation;

DOI:10.1021/jm4014373

upstream raw materials:

glycolic Acid

3-(4-(3-aminopropoxy)-3,5-dimethylphenyl)-1-((3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophen-1-yl)propan-1-one

(+)-Δ³-carene

(3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid

Refernces

• 1、 -. "NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS". . . Retrieved 2011/10/01.