Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

Base Information

Chemical Name:Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester
CAS No.:186809-16-5
Molecular Formula:C₂₃H₃₃NO₄Si
Molecular Weight:415.605
Hs Code.:

Synonyms:Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

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Chemical Property of Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

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Technology Process of Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

There total 11 articles about Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester 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: 98.0%

: 108-24-7
acetic anhydride

: 186809-14-3
(3S,4R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-7-ynenitrile

: 186809-16-5
Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

Guidance literature:: With dmap; TEA; In dichloromethane;
DOI:10.1021/ja963900h

Reference yield: 86.0%

: 64-19-7,77671-22-8
acetic acid

: 186809-15-4
(3S,4R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-7-ynenitrile

: 186809-16-5
Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

Guidance literature:: With pyridine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -45 - 20 ℃;
DOI:10.1021/ja963900h

Reference yield:

: (3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-7-ynenitrile

: 186809-16-5
Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / Jones reagent / acetone / 0 °C

2: LiAlH₄; Darvon alcohol / -78 °C

3: 98 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; jones reagent; Darvon alcohol; triethylamine; In dichloromethane; acetone; 1: Oxidation / 2: Reduction / 3: Acetylation;
DOI:10.1021/ja970839n