{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

Base Information

Chemical Name:{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane
CAS No.:1391973-91-3
Molecular Formula:C₃₅H₅₆O₅Si₂
Molecular Weight:612.998
Hs Code.:

Synonyms:{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

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Chemical Property of {[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

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Technology Process of {[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

There total 6 articles about {[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane 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: 90.0%

: 1391973-90-2
(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(prop-2-en-1-yl)oxan-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1391973-91-3
{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 42h; Inert atmosphere;
DOI:10.1002/anie.201201826

Reference yield:

: [(3aR,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-2-(iodomethyl)-hexahydro-2H-furo[3,2-b]pyran-5-yl]methanol

: 1391973-91-3
{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1: chloro-trimethyl-silane / tetrahydrofuran; water; ethylene dibromide / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

With 1H-imidazole; chloro-trimethyl-silane; In tetrahydrofuran; water; ethylene dibromide; N,N-dimethyl-formamide;
DOI:10.1002/anie.201201826

Reference yield:

: C₆H₁₀O₆

: 1391973-91-3
{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / Inert atmosphere; Cooling with ice

1.2: 15 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 22 h / 0 - 20 °C / Inert atmosphere

3.1: iodine / dichloromethane / 0.92 h / 0 °C / Inert atmosphere

4.1: chloro-trimethyl-silane / tetrahydrofuran; water; ethylene dibromide / 1 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

With 1H-imidazole; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; iodine; sodium hydride; In tetrahydrofuran; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1002/anie.201201826