(1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one

Base Information

• Chemical Name: (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one
• CAS No.: 1040833-53-1
• Molecular Formula: C₂₆H₃₄O₄Si
• Molecular Weight: 438.639

Synonyms:(1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one

Chemical Property of (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one

Chemical Property:

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Technology Process of (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one

There total 2 articles about (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one 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: 90.0%

C26H32O4Si (1040834-07-8) → (1R,5S)-1-[(1R)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1040833-50-8) + (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1040833-53-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.416667h;

DOI:10.1002/anie.200800253

Reference yield: 80.0%

C10H16O4 + tert-butylchlorodiphenylsilane (58479-61-1) → (1R,5S)-1-[(1R)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1040833-50-8) + (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1040833-53-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1002/anie.200800253

Reference yield: 97.0%

(1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-hydroxyethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1040833-53-1) + O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-(4-methoxyphenylmethoxy)ethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one (1186088-72-1)

Guidance literature:

With trifluorormethanesulfonic acid; In diethyl ether; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo9012546

upstream raw materials:

tert-butylchlorodiphenylsilane

C₂₆H₃₂O₄Si

Downstream raw materials:

C₂₆H₃₂O₄Si

(1R,5S)-1-[(1S)-2-tert-butydiphenylsilyloxy-1-(4-methoxyphenylmethoxy)ethyl]-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one

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