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

Base Information

• Chemical Name: tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate
• CAS No.: 1345017-45-9
• Molecular Formula: C₃₃H₄₃NO₄Si
• Molecular Weight: 545.794

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

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

Chemical Property:

Purity/Quality:

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

There total 5 articles about tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-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: 98.0%

(1S,2R)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester (1042339-01-4) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate (1345017-45-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

benzyl bromide (100-39-0) → tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate (1345017-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

3: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate (114301-34-7,114301-35-8,117487-60-2,122709-37-9,117487-58-8) → tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate (1345017-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

3: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2011.08.084

upstream raw materials:

(1S,2R)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester

tert-butylchlorodiphenylsilane

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

benzyl bromide

Downstream raw materials:

tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

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