(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

Base Information

Chemical Name:(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile
CAS No.:186809-13-2
Molecular Formula:C₁₉H₂₉NO₃Si
Molecular Weight:347.53
Hs Code.:

Synonyms:(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

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Chemical Property of (3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

Chemical Property:

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Technology Process of (3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

There total 7 articles about (3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile 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: 96.0%

: 186809-12-1
(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-hexanenitrile

: 186809-13-2
(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

Guidance literature:: With Swern ox;
DOI:10.1021/ja963900h

Reference yield:

: 110009-21-7,115586-66-8,110044-33-2
(S)-2-((R)-1-benzyloxy-allyl)-oxirane

: 186809-13-2
(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / methanol / 2.5 h / 70 °C

2.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

3.2: 88 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / -20 - 20 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / -78 - -65 °C

4.2: 96 percent / triethylamine / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; bis-(1,2-dimethylpropyl)borane; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Ring cleavage / 2.1: silylation / 3.1: hydroboration / 3.2: Oxidation / 4.1: Oxidation / 4.2: Oxidation;
DOI:10.1021/ja970839n

Reference yield:

: 186809-10-9
(3S,4R)-4-Benzyloxy-3-hydroxy-hex-5-enenitrile

: 186809-13-2
(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexanenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C

2.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

2.2: 88 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / -20 - 20 °C

3.1: oxalyl chloride; DMSO / CH₂Cl₂ / -78 - -65 °C

3.2: 96 percent / triethylamine / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; bis-(1,2-dimethylpropyl)borane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: hydroboration / 2.2: Oxidation / 3.1: Oxidation / 3.2: Oxidation;
DOI:10.1021/ja970839n