(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene

Base Information

• Chemical Name: (1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene
• CAS No.: 127783-19-1
• Molecular Formula: C₂₂H₃₁BrO₅Si
• Molecular Weight: 483.475

Synonyms:(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene

Chemical Property of (1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene

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Technology Process of (1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene

There total 1 articles about (1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene 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: 91.0%

bromomethyldimethylsilyl chloride (16532-02-8) + Methyl 4,6-O-Benzylidene-2,3-dideoxy-3,2-C-<(3'R)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside (127910-93-4) → (1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.02,7>-tetradec-10-ene (127783-19-1)

Guidance literature:

With triethylamine;

DOI:10.1039/c39900000148

Reference yield: 82.0%

(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.02,7>-tetradec-10-ene (127783-19-1) → (1R,2S,4R,7R,9S,10R,11S,15R)-9-methoxy-1,13,13-trimethyl-4-phenyl-3,5,8,14-tetraoxa-13-silatetracyclo<8.7.0.02,7011,15>heptadecane (127783-20-4,127854-55-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1039/c39900000148

Reference yield:

(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.02,7>-tetradec-10-ene (127783-19-1) → (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.02,7>-tetradecan-12-ol (127818-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / azoisobutyronitrile, tributylstannane / benzene / 2 h / Heating

2: 69 percent / KF, 30percent aq. H₂O₂ / dimethylformamide / 24 h / Ambient temperature

With potassium fluoride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; benzene;

upstream raw materials:

bromomethyldimethylsilyl chloride

Methyl 4,6-O-Benzylidene-2,3-dideoxy-3,2-C-<(3'R)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside

Downstream raw materials:

(1R,2S,4R,7R,9S,10R,11S,15R)-9-methoxy-1,13,13-trimethyl-4-phenyl-3,5,8,14-tetraoxa-13-silatetracyclo<8.7.0.0^2,70^11,15>heptadecane

(1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol

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