Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane

Base Information

• Chemical Name: Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane
• CAS No.: 188953-81-3
• Molecular Formula: C₂₁H₂₉BrO₅Si
• Molecular Weight: 469.448
• Mol file: 188953-81-3.mol

Synonyms:Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane

Chemical Property of Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]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,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane

There total 2 articles about Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]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: 89.0%

bromomethyldimethylsilyl chloride (16532-02-8) + (2R,4aR,6S,8S,9aR,9bS)-6-Methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-ol (188953-84-6) → Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane (188953-81-3)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(97)00211-6

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside (171076-03-2) → Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane (188953-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LS-Selectide

2: 89 percent / Et₃N / CH₂Cl₂

With lithium tri-sec-butyl(hydrido)borate; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(97)00211-6

Reference yield:

Bromomethyl-((2R,4aR,6S,8S,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane (188953-81-3) → (2R,4aR,6S,6aS,7S,8S,9aR,9bS)-8-(tert-Butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-9a-methyl-2-phenyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine

Guidance literature:

Multi-step reaction with 3 steps

1: Bu₃SnH

2: 1.) NaCNBH₃, AIBN, 2.) H₂O₂ / 1.) t-BuOH, 15 h, 90 deg C, 2.) THF, MeOH, reflux, 15 h

3: 94 percent / imidazole, DMAP / CH₂Cl₂

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium cyanoborohydride; In dichloromethane;

DOI:10.1016/S0040-4039(97)00211-6

upstream raw materials:

bromomethyldimethylsilyl chloride

(2R,4aR,6S,8S,9aR,9bS)-6-Methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-ol

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

Downstream raw materials:

(2R,4aR,6S,6aS,6bR,9aS,10aR,10bS)-6-Methoxy-8,8,10a-trimethyl-2-phenyl-decahydro-1,3,5,9-tetraoxa-8-sila-pentaleno[2,1-a]naphthalene

(2R,4aR,6S,6aS,7S,8S,9aR,9bS)-7-Hydroxymethyl-6-methoxy-9a-methyl-2-phenyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-ol