(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol

Base Information

Chemical Name:(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol
CAS No.:886852-60-4
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

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

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

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

There total 6 articles about (2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-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%

: 886852-59-1
(2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one

: 886852-60-4
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 4h;
DOI:10.1021/ol0602811

Reference yield:

: 886852-56-8
(2S)-6-hydroxy-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one

: 886852-60-4
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / DMAP / CH₂Cl₂ / 14 h / -78 °C

2: 88 percent / Pd₂(DBA)3*CHCl₃; triphenylphosphine / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 94 percent / NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 °C

With dmap; sodium tetrahydroborate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In methanol; dichloromethane; 3: Luche reduction;
DOI:10.1021/ol0602811

Reference yield:

: 886852-57-9
(S)-1-(furan-2-yl)-4-tert-butyldimethylsilyloxybutan-1-ol

: 886852-60-4
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / NBS; H₂O; NaHCO₃ / NaOAc*3H₂O / tetrahydrofuran / 0.5 h / 0 °C

2: 85 percent / DMAP / CH₂Cl₂ / 14 h / -78 °C

3: 88 percent / Pd₂(DBA)3*CHCl₃; triphenylphosphine / CH₂Cl₂ / 2 h / 0 - 20 °C

4: 94 percent / NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; water; sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium acetate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1: Achmatowicz reaction / 4: Luche reduction;
DOI:10.1021/ol0602811