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

Base Information

Chemical Name:(2R,4S,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-hexahydro-pyrano[3,2-b]pyran-3-one
CAS No.:328535-26-8
Molecular Formula:C₂₇H₄₂O₆Si
Molecular Weight:490.712
Hs Code.:

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

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

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

There total 5 articles about (2R,4S,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-hexahydro-pyrano[3,2-b]pyran-3-one 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: 89.0%

: 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

: 328535-26-8
(2R,4S,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 1.5h;
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

: 328535-26-8
(2R,4S,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: Multi-step reaction with 5 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

5.1: 89 percent / DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 1.5 h / -78 °C

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

Reference yield:

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

: 328535-26-8
(2R,4S,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 573 mg / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

2: 89 percent / DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 1.5 h / -78 °C

With dmap; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane;
DOI:10.1021/jo001433n