(E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

Base Information

• Chemical Name: (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol
• CAS No.: 247200-04-0
• Molecular Formula: C₄₀H₇₆O₆Si₂
• Molecular Weight: 709.211

Synonyms:(E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

Chemical Property of (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

Chemical Property:

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Technology Process of (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

There total 2 articles about (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol 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: 83.0%

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal (204572-66-7) + Tributyl-((E)-(R)-1-methoxymethoxy-undec-2-enyl)-stannane → (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol (247200-04-0)

Guidance literature:

With indium(III) chloride; In ethyl acetate; at -78 - 20 ℃; for 3h;

DOI:10.1021/np990132+

Reference yield: 80.0%

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal (204572-66-7) + Tributyl-((E)-(R)-1-methoxymethoxy-undec-2-enyl)-stannane → (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol (247200-04-0) + (E)-(4R,5R,8R,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

Guidance literature:

With indium(III) bromide; In ethyl acetate; at -78 - 20 ℃;

DOI:10.1021/jo026433x

Reference yield: 94.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol (247200-04-0) → Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester (247200-05-1)

Guidance literature:

In pyridine; for 12h;

DOI:10.1021/np990132+

upstream raw materials:

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal

Downstream raw materials:

Toluene-4-sulfonic acid (E)-(1S,2R)-1-[(3R,4R)-7-benzyloxy-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-heptyl]-2-methoxymethoxy-dodec-3-enyl ester

(+)-asimicin

asimin

Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester

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