Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

Base Information

• Chemical Name: Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane
• CAS No.: 161821-32-5
• Molecular Formula: C₂₀H₂₉BrO₅Si
• Molecular Weight: 457.437
• Mol file: 161821-32-5.mol

Synonyms:

Chemical Property of Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

There total 2 articles about Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane 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:

(2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (114047-68-6) → Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane (161821-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaBH₄, CeCl₃ / ethanol

2: Et₃N / CH₂Cl₂

With sodium tetrahydroborate; cerium(III) chloride; triethylamine; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)73076-0

Reference yield:

bromomethyldimethylsilyl chloride (16532-02-8) + (2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (161821-24-5) → Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane (161821-32-5)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)73076-0

Reference yield: 20.0%

Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane (161821-32-5) → [(2R,4aR,6S,8R,8aR)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-trimethyl-silane + (3R,4aR,4bR,8R,8aR,9S,10aR)-8-Ethyl-9-methoxy-6,6-dimethyl-3-phenyl-octahydro-2,4,5,10-tetraoxa-6-sila-phenanthrene

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

DOI:10.1016/S0040-4039(00)73076-0

upstream raw materials:

bromomethyldimethylsilyl chloride

(2R,4aR,6S,8R,8aS)-6-Methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

(2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one