(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

Base Information

• Chemical Name: (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide
• CAS No.: 160796-76-9
• Molecular Formula: C₂₇H₃₉BrO₆
• Molecular Weight: 539.507

Synonyms:(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

Chemical Property of (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

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Technology Process of (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

There total 1 articles about (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide 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%

1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) + (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5,9,11-tetrahydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide (119870-68-7) → (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide (160796-76-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/ja00104a010

Reference yield: 100.0%

(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide (160796-76-9) → (2R,3S,4R,5S,6S,8R,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; Ambient temperature;

DOI:10.1021/ja00104a010

Reference yield: 78.0%

(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-9,11-dihydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide (160796-76-9) → (2R,3S,4R,5S,6S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-11-hydroxy-2,4,6,10,12,13-hexamethyl-8-methylene-9-oxotetradecanolide

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/ja00104a010

upstream raw materials:

1,1-dimethoxy-1-(4-bromophenyl)methane

(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5,9,11-tetrahydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

Downstream raw materials:

(2R,3S,4R,5S,6S,8S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide

(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

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