(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

Base Information

Chemical Name:(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane
CAS No.:270571-08-9
Molecular Formula:C₂₈H₃₇NO₄Si
Molecular Weight:479.692
Hs Code.:

Synonyms:(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

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Chemical Property of (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

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Technology Process of (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

There total 3 articles about (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane 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: 88.0%

: 151-50-8
potassium cyanide

: 58479-61-1
tert-butylchlorodiphenylsilane

: 270571-07-8
(2S,3R,4R)-2,3-epoxy-4,5-(cyclohexylidenedioxy)pentan-1-ol

: 270571-08-9
(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

Guidance literature:: potassium cyanide; (2S,3R,4R)-2,3-epoxy-4,5-(cyclohexylidenedioxy)pentan-1-ol; With titanium(IV) isopropylate; tetra-(n-butyl)ammonium iodide; In dimethyl sulfoxide; at 20 ℃; for 60h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Further stages.;
DOI:10.1021/jo9917700

Reference yield:

: 124988-77-8
(2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-prop-2-en-1-ol

: 270571-08-9
(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH₂Cl₂; decane / 16 h / -15 °C

2.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C

2.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; In decane; dichloromethane; dimethyl sulfoxide; 1.1: Sharpless asymmetric epoxidation / 2.1: Ring cleavage / 2.2: silylation;
DOI:10.1021/jo9917700

Reference yield:

: (E)-(S)-3-(1,4-Dioxa-spiro[4.5]dec-2-yl)-acrylic acid methyl ester

: 270571-08-9
(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / DIBAL / toluene; CH₂Cl₂ / 2 h / 20 °C

2.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH₂Cl₂; decane / 16 h / -15 °C

3.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C

3.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In decane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Reduction / 2.1: Sharpless asymmetric epoxidation / 3.1: Ring cleavage / 3.2: silylation;
DOI:10.1021/jo9917700