(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Base Information

Chemical Name:(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile
CAS No.:375826-90-7
Molecular Formula:C₂₅H₄₁NO₄Si
Molecular Weight:447.69
Hs Code.:

Synonyms:(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Chemical Property of (6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Chemical Property:

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

There total 11 articles about (6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile 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: 75.0%

: 151-50-8
potassium cyanide

: 77-76-9
2,2-dimethoxy-propane

: (4R,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-heptanoic acid ethyl ester

: 375826-90-7
(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multistep reaction;
DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D

Reference yield:

: 375826-96-3
(2S,3S)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-methylpentanoic acid ethyl ester

: 375826-90-7
(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: DIBAL-H / CH₂Cl₂ / 1.17 h / -78 °C

2.1: 1.29 g / SnCl₂ / CH₂Cl₂ / 18 h

3.1: NaBH₄ / methanol / 2 h / -50 °C

4.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h

5.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

6.1: KCN/18-crown-6 complex / CH₂Cl₂ / 12 h

6.2: 0.342 g / H₂O; dl-camphorsulfonic acid / acetone; CH₂Cl₂ / 18 h

With dmap; potassium cyanide; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; tin(ll) chloride; In methanol; dichloromethane; 2.1: Roskamp homologation;
DOI:10.1016/S0040-4020(02)00666-X

Reference yield:

: 375826-97-4
(4S,5S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4-methyl-3-oxoheptanoic acid ethyl ester

: 375826-90-7
(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaBH₄ / methanol / 2 h / -50 °C

2.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h

3.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

4.1: KCN/18-crown-6 complex / CH₂Cl₂ / 12 h

4.2: 0.342 g / H₂O; dl-camphorsulfonic acid / acetone; CH₂Cl₂ / 18 h

With dmap; potassium cyanide; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(02)00666-X