(1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester

Base Information

• Chemical Name: (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester
• CAS No.: 915098-62-3
• Molecular Formula: C₂₅H₃₅N₃O₃Si₂
• Molecular Weight: 481.742
• Mol file: 915098-62-3.mol

Synonyms:

Chemical Property of (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester

There total 4 articles about (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester 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:

cyclopent-3-enecarboxylic acid tert-butyldiphenylsilyl ester (915098-60-1) → (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester (915098-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: m-CPBA / CH₂Cl₂ / 0 - 20 °C

2.1: Jacobsen's chromium(III) salen catalyst / diethyl ether / 0.25 h

2.2: diethyl ether / 72 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; In diethyl ether; dichloromethane;

DOI:10.1016/j.tetasy.2006.07.001

Reference yield:

3-cyclopentene-1-carboxylic acid (7686-77-3) → (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester (915098-62-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / DIPEA; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2.1: m-CPBA / CH₂Cl₂ / 0 - 20 °C

3.1: Jacobsen's chromium(III) salen catalyst / diethyl ether / 0.25 h

3.2: diethyl ether / 72 h / 20 °C

With dmap; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; In diethyl ether; dichloromethane;

DOI:10.1016/j.tetasy.2006.07.001

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid tert-butyldiphenylsilyl ester (915098-62-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / DIPEA; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2.1: m-CPBA / CH₂Cl₂ / 0 - 20 °C

3.1: Jacobsen's chromium(III) salen catalyst / diethyl ether / 0.25 h

3.2: diethyl ether / 72 h / 20 °C

With dmap; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; In diethyl ether; dichloromethane;

DOI:10.1016/j.tetasy.2006.07.001

upstream raw materials:

3,4-epoxycyclopentanecarboxylic acid tert-butyldiphenylsilyl ester

trimethylsilylazide

cyclopent-3-enecarboxylic acid tert-butyldiphenylsilyl ester

3-cyclopentene-1-carboxylic acid