tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Base Information

Chemical Name:tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane
CAS No.:197164-78-6
Molecular Formula:C₄₆H₆₆O₅SSi
Molecular Weight:759.179
Hs Code.:

Synonyms:tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

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Chemical Property of tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

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Technology Process of tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

There total 6 articles about tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane 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: 92.0%

: 100-39-0
benzyl bromide

: 197164-76-4
(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 197164-78-6
tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 18h; Ambient temperature;
DOI:10.1021/jo971233k

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 197164-78-6
tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / pyridine / 18 h / Ambient temperature

2: 92 percent / NaH / dimethylformamide / 18 h / Ambient temperature

With sodium hydride; In pyridine; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k

Reference yield:

: Dicyclohexyl-methanethiol

: 197164-78-6
tert-Butyl-dimethyl-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 49 percent / TMSOTf / CH₂Cl₂ / 16 h / Ambient temperature

2: 100 percent / NaOMe / CH₂Cl₂; methanol / 3 h

3: 76 percent / pyridine / 18 h / Ambient temperature

4: 92 percent / NaH / dimethylformamide / 18 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k