(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

Base Information

Chemical Name:(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate
CAS No.:1138325-28-6
Molecular Formula:C₂₆H₃₈O₈SSi
Molecular Weight:538.734
Hs Code.:

Synonyms:(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

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Chemical Property of (R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

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Technology Process of (R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

There total 3 articles about (R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate 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%

: 1138325-27-5
(R)-2-(benzyloxy)-1-((4S,5S)-5-((R)-2-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

: 1138325-28-6
(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

Guidance literature:: With 10% Pd/C; hydrogen; In ethanol; for 72h; under 3102.97 Torr;
DOI:10.1021/jo900030p

Reference yield:

: 847659-89-6
(4S,4'S,5R,5'R)-5'-(tert-butyldiphenylsilyloxy)-2,2'-diphenyl-4,4'-bi(1,3-dioxan)-5-yl methanesulfonate

: 1138325-28-6
(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: camphor-10-sulfonic acid / acetone / 20 °C / Inert atmosphere

3: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 3102.97 Torr

With triethylsilane; palladium 10% on activated carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; In ethanol; dichloromethane; acetone;
DOI:10.1002/ejoc.201100968

Reference yield:

: 847659-90-9
(2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate

: 1138325-28-6
(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid / acetone / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 3102.97 Torr

With palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; In ethanol; acetone;
DOI:10.1002/ejoc.201100968