(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Base Information

Chemical Name:(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
CAS No.:862602-87-7
Molecular Formula:C₂₂H₂₈O₄Si
Molecular Weight:384.547
Hs Code.:

Synonyms:(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

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Chemical Property of (4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Chemical Property:

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Technology Process of (4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

There total 4 articles about (4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-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:

: 862603-51-8
6-(tert-butyl-diphenyl-silanyloxy)-hex-3-enoic acid methyl ester

: 862602-87-7
(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

: 949013-62-1
(4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Guidance literature:: With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 20h; Title compound not separated from byproducts;
DOI:10.1021/ja0526867

Reference yield:

: 127793-62-8
4-((tert-butyldiphenylsilyl)oxy)butanal

: 862602-87-7
(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / Et₃N / 90 °C

2: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

With AD-mix-α; methanesulfonamide; triethylamine; In water; tert-butyl alcohol; 1: Knoevenagel condensation / 2: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0526867

Reference yield:

: 130372-07-5
4-(tret-butyldiphenylsilyloxy)butan-1-ol

: 862602-87-7
(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 84 percent / Et₃N / 90 °C

3: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

With AD-mix-α; oxalyl dichloride; methanesulfonamide; dimethyl sulfoxide; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Swern oxidation / 2: Knoevenagel condensation / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0526867