(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate

Base Information

Chemical Name:(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate
CAS No.:886852-61-5
Molecular Formula:C₂₃H₃₆O₆Si
Molecular Weight:436.621
Hs Code.:

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

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

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

There total 7 articles about (2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate 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: 72.0%

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

: 79-22-1
methyl chloroformate

: 886852-61-5
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ol0602811

Reference yield:

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

: 886852-61-5
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate

Guidance literature:: Multi-step reaction with 4 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

4: 72 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 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

: 886852-61-5
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate

Guidance literature:: Multi-step reaction with 5 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

5: 72 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 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