(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane
CAS No.:139277-18-2
Molecular Formula:C₂₅H₄₄O₃SSi₂
Molecular Weight:480.86
Hs Code.:

Synonyms:(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

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Chemical Property of (1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

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Technology Process of (1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

There total 4 articles about (1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139277-09-1
(1R,2S,3R,4S,6R)-6-Hydroxymethyl-3-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

: 139277-18-2
(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 48h; Ambient temperature;
DOI:10.1021/jo00033a002

Reference yield:

: 24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2
(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

: 139277-18-2
(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / CHCl₃ / 48 h / 0 deg C to r.t.

2: 90 percent / LAH / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00033a002

Reference yield:

: 139277-16-0
(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

: 139277-18-2
(1S,2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / LAH / tetrahydrofuran / 1 h / 0 °C

2: 95 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo00033a002