(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate
CAS No.:948036-06-4
Molecular Formula:C₃₁H₄₄O₇Si
Molecular Weight:556.772
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

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Chemical Property of (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

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Technology Process of (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

There total 4 articles about (2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate 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: 62.0%

: 948036-05-3
(2S,3S,4S,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-4-trifluoromethanesulfonyloxy-tetrahydro-4H-pyran

: 3396-11-0
cesium acetate

: 948036-06-4
(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

Guidance literature:: With 18-crown-6 ether; In toluene; at 30 ℃; for 24h; sonication;
DOI:10.1016/j.tetlet.2007.06.057 DOI:10.1016/j.tet.2008.06.068

Reference yield:

: 948036-04-2
(2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

: 948036-06-4
(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / pyridine / 2.5 h / -20 - 20 °C

2: 62 percent / 18-crown-6 / toluene / 24 h / 30 °C / sonication

With pyridine; 18-crown-6 ether; In toluene;
DOI:10.1016/j.tetlet.2007.06.057

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 948036-06-4
(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2: 93 percent / pyridine / 2.5 h / -20 - 20 °C

3: 62 percent / 18-crown-6 / toluene / 24 h / 30 °C / sonication

With pyridine; 1H-imidazole; 18-crown-6 ether; In dichloromethane; toluene;
DOI:10.1016/j.tetlet.2007.06.057