(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol
CAS No.:81389-87-9
Molecular Formula:C₁₉H₃₀O₄Si
Molecular Weight:350.53
Hs Code.:

Synonyms:(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

There total 11 articles about (2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol 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: 94.0%

: 81389-86-8
(2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 81389-87-9
(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 5h;
DOI:10.1016/j.tet.2009.07.088

Reference yield: 83.0%

: 81389-89-1
benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

: 81389-87-9
(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at -78 ℃; for 3h; diastereoselective reaction;
DOI:10.1021/ja305321e

Reference yield:

: 2873-29-2
D-glucal triacetate

: 81389-87-9
(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: FeCl₃ / CH₂Cl₂ / 0.25 h

1.2: Na / methanol / 2 h

2.1: 92 percent / imidazole / CH₂Cl₂ / 3 h / 0 °C

With 1H-imidazole; iron(III) chloride; In dichloromethane; 1.1: Ferrier rearrangement;
DOI:10.1081/CAR-120014904