(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

Chemical Name:(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:328535-19-9
Molecular Formula:C₂₇H₄₄O₆Si
Molecular Weight:492.728
Hs Code.:

Synonyms:(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

There total 4 articles about (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-hydroxymethyl-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

: 328535-19-9
(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/jo001433n

Reference yield:

: 194039-11-7
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

: 328535-19-9
(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.58 h / Heating

1.2: 93 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 1.91 g / oxalyl chloride; DMSO / CH₂Cl₂ / 1.5 h / -78 °C

3.1: camphorsulfonic acid / benzene / 7 h / Heating

4.1: 573 mg / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

With dmap; oxalyl dichloride; camphor-10-sulfonic acid; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/jo001433n

Reference yield:

: 328534-81-2
1-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-hept-6-en-3-ol

: 328535-19-9
(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.91 g / oxalyl chloride; DMSO / CH₂Cl₂ / 1.5 h / -78 °C

2: camphorsulfonic acid / benzene / 7 h / Heating

3: 573 mg / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

With dmap; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene;
DOI:10.1021/jo001433n