tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate
• CAS No.: 1345017-64-2
• Molecular Formula: C₃₀H₃₉NO₅Si
• Molecular Weight: 521.729

Synonyms:tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate

Chemical Property of tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate

Chemical Property:

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Technology Process of tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate

There total 2 articles about tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-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: 80.0%

(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate (1345017-63-1) → tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate (1345017-64-2)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxyocta-3,7-dien-2-ylcarbamate (1345017-50-6) → tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate (1345017-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / 24 h / 20 °C / Inert atmosphere

With Grubbs catalyst first generation; dmap; triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield: 90.0%

tert-butyl (R,E)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)pent-3-en-2-ylcarbamate (1345017-64-2) → tert-butyl (R)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-tetrahydrofuran-2-yl)pentan-2-ylcarbamate (1345017-65-3)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2011.08.084

upstream raw materials:

tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxyocta-3,7-dien-2-ylcarbamate

(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

Downstream raw materials:

tert-butyl (R)-1-(tert-butyldiphenylsilyloxy)-5-((R)-5-oxo-tetrahydrofuran-2-yl)pentan-2-ylcarbamate

tert-butyl (2R,6R)-1-(tert-butyldiphenylsilyloxy)-6,9-dihydroxynonan-2-ylcarbamate

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