(1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane

Base Information

• Chemical Name: (1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane
• CAS No.: 183065-57-8
• Molecular Formula: C₁₅H₃₃N₃O₂Si₂
• Molecular Weight: 343.617
• Mol file: 183065-57-8.mol

Synonyms:(1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane

Chemical Property of (1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane

There total 1 articles about (1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane 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:

ethyl 3-cyclopentene-1-carboxylate (21622-01-5) → (1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane (183065-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70.5 percent / MCPBA / CH₂Cl₂ / 4 h / Ambient temperature

2: 97 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

3: 14.28 g / imidazole / CH₂Cl₂

4: (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2 / diethyl ether / 24 h / Ambient temperature; other reagent

With 1H-imidazole; lithium aluminium tetrahydride; (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo961241l

Reference yield:

(1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane (183065-57-8) → ((1S,3R)-3-Azido-4-phenylselanyl-cyclopentylmethoxy)-tert-butyl-dimethyl-silane

Guidance literature:

Multi-step reaction with 3 steps

1: (1S)-(+)-10-camphorsulfonic acid / methanol

2: 19.62 g / CH₂Cl₂ / Ambient temperature

3: tetrahydrofuran; hexamethylphosphoric acid triamide / 4.5 h / Heating

With (+)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/jo961241l

Reference yield:

(1R,2R,4S)-1-Azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-cyclopentane (183065-57-8) → Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester (233588-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (1S)-(+)-10-camphorsulfonic acid / methanol

2: 19.62 g / CH₂Cl₂ / Ambient temperature

With (+)-10-camphorsulfonic acid; In methanol; dichloromethane;

DOI:10.1021/jo961241l

upstream raw materials:

ethyl 3-cyclopentene-1-carboxylate

Downstream raw materials:

Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester