(3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene

Base Information

• Chemical Name: (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene
• CAS No.: 123827-57-6
• Molecular Formula: C₂₉H₃₃N₃O₂Si
• Molecular Weight: 483.685
• Mol file: 123827-57-6.mol

Synonyms:(3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene

Chemical Property of (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene

There total 2 articles about (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene 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: 81.0%

(3S,4S)-3-(benzyloxy)-4-<(methylsulfonyl)oxy>-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene → (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene (123827-57-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 130 ℃; for 7h;

DOI:10.1246/bcsj.62.1355

Reference yield:

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene (115435-01-3) → (3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene (123827-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 1 h / Ambient temperature

2: 81 percent / sodium azide / dimethylformamide / 7 h / 130 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;

DOI:10.1246/bcsj.62.1355

Reference yield: 99.0%

(3S,4R)-4-azido-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-1-cyclopentene (123827-57-6) → (3S,4R)-4-azido-3-(benzyloxy)-1-cyclopentene-1-methanol (123827-58-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.62.1355

upstream raw materials:

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

Downstream raw materials:

(3S,4R)-4-azido-3-(benzyloxy)-1-cyclopentene-1-methanol

(+)-cyclaradine

(1R,2R,3R,4R)-1-acetamido-3-acetoxy-4-(acetoxymethyl)-2-(benzyloxy)cyclopentane

(1R,2R,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol