(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane
CAS No.:465545-55-5
Molecular Formula:C₂₄H₃₉NO₄Si
Molecular Weight:433.663
Hs Code.:

Synonyms:(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

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Chemical Property of (4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

Chemical Property:

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Technology Process of (4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

There total 5 articles about (4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane 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:

: 86864-60-0
2-(tert-butyldimethylsilyloxy)ethyl bromide

: 465545-54-4
(6R)-4-cyano-6-(2-benzyloxy)-ethyl-2,2-dimethyl-1,3-dioxane

: (4R,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

: 465545-55-5
(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -40 ℃; for 0.416667h; Title compound not separated from byproducts.;
DOI:10.1021/ol0263550

Reference yield:

: (R)-6-Benzyloxy-2-hydroxy-4-trimethylsilanyloxy-hexanenitrile

: 465545-55-5
(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1: dl-CSA / acetone; diethyl ether; H₂O / 24 h / 20 °C

2: LDA / tetrahydrofuran / 0.42 h / -40 °C

With DL-10-camphorsulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; acetone;
DOI:10.1021/ol0263550

Reference yield:

: 113335-04-9
(R)-5-Benzyloxy-3-hydroxy-pentanoic acid ethyl ester

: 465545-55-5
(4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 steps

1.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

2.1: DIBALH / diethyl ether; toluene / 0.83 h / -78 °C

3.1: 18-crown-6; KCN / diethyl ether / 17 h

3.2: 3 h / 20 °C

4.1: dl-CSA / acetone; diethyl ether; H₂O / 24 h / 20 °C

5.1: LDA / tetrahydrofuran / 0.42 h / -40 °C

With dmap; potassium cyanide; 18-crown-6 ether; DL-10-camphorsulfonic acid; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene;
DOI:10.1021/ol0263550