tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate
• CAS No.: 1315158-32-7
• Molecular Formula: C₂₆H₃₅NO₄Si
• Molecular Weight: 453.654
• Mol file: 1315158-32-7.mol

Synonyms:tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

Chemical Property of tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

There total 5 articles about tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate 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: 97.0%

tert-butyl (2S,3R)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypent-4-en-2-ylcarbamate (1020409-56-6) → tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate (1315158-32-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1055/s-0032-1317962

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate (1315158-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / dichloromethane / 3 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

With 1H-imidazole; Dess-Martin periodane; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2011.05.103

Reference yield:

tert-butyl (S)-4-[(R)-1-(tert-butyldiphenylsilyloxy)allyl]-2,2-dimethyloxazolidine-3-carboxylate (1315158-29-2) → tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate (1315158-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

With Dess-Martin periodane; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2011.05.103

upstream raw materials:

tert-butyl (2S,3R)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypent-4-en-2-ylcarbamate

tert-butyl (S)-4-[(R)-1-(tert-butyldiphenylsilyloxy)allyl]-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₂₆H₃₅NO₄Si

C₂₆H₃₅NO₄Si

C₂₆H₃₇NO₆Si

C₂₆H₃₇NO₆Si