(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

Base Information

Chemical Name:(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate
CAS No.:153321-78-9
Molecular Formula:C₂₆H₃₆O₅Si
Molecular Weight:456.654
Hs Code.:

Synonyms:(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

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Technology Process of (3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

There total 3 articles about (3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate 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:

: 92808-78-1
(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

: 153321-78-9
(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: t-BuOOH, Ti(OiPr)4, opt. active diisopropyl tartrate, activated molecular sieves 3 Angstroem / CH₂Cl₂ / 36 h / -20 °C

2: 80 percent / pyridine sulfur trioxide complex, DMSO, NEt₃ / CH₂Cl₂ / 0.5 h

3: 1.35 g / diethyl ether / 0.25 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; D-diisopropyl tartrate; 3 A molecular sieve; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)82375-9

Reference yield:

: 131484-40-7
((2S,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol

: 153321-78-9
(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / pyridine sulfur trioxide complex, DMSO, NEt₃ / CH₂Cl₂ / 0.5 h

2: 1.35 g / diethyl ether / 0.25 h / -78 °C

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)82375-9

Reference yield:

: 74786-02-0
1-(tert-butyldimethylsilyloxy)-1-tert-butoxyethylene

: 131486-44-7
(2R,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxirane-2-carbaldehyde

: 153321-78-9
(3S,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

: 153321-79-0
(3R,4S,5S)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

: (S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-propionic acid tert-butyl ester

: (R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-propionic acid tert-butyl ester

Guidance literature:: With bismuth(III) chloride; zinc(II) iodide; In dichloromethane; for 12h; Yield given. Yields of byproduct given;
DOI:10.1007/BF00807077