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

Base Information

Chemical Name:(3S,4R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-7-ynenitrile
CAS No.:186809-15-4
Molecular Formula:C₂₁H₃₁NO₃Si
Molecular Weight:373.568
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 8 articles about (3S,4R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-7-ynenitrile 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:

: 191787-58-3
(3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-oct-7-ynenitrile

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

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

Guidance literature:: With lithium aluminium tetrahydride; ent-Darvon alcohol; at -78 ℃;
DOI:10.1021/ja970839n

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: LiAlH₄; Darvon alcohol / -78 °C

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

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / NaH, TBAI / tetrahydrofuran / -20 - 20 °C

2: 93 percent / methanol / Heating

3: 94 percent / imidazole / dimethylformamide / 0 - 20 °C

4: 1.) disiamylborane, 2.) NaOH, H₂O₂ / 1.) THF, 0-20 deg C

5: 96 percent / Swern ox

6: CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; sodium hydroxide; Swern ox; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja963900h