(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol

Base Information

• Chemical Name: (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol
• CAS No.: 1184762-67-1
• Molecular Formula: C₃₉H₇₄O₆Si₂
• Molecular Weight: 695.184

Synonyms:(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol

Chemical Property of (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol

Chemical Property:

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Technology Process of (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol

There total 1 articles about (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol 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: 29.0%

(Z)-(2R,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-4,6,8,10,12-pentamethyl-2-oxiranyltridec-8-en-3-ol (1184762-66-0) → (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol (1184762-67-1)

Guidance literature:

(Z)-(2R,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-4,6,8,10,12-pentamethyl-2-oxiranyltridec-8-en-3-ol; With periodic acid dihydrate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 16h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1002/anie.200901740

Reference yield: 86.0%

(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-ene-1,3-diol (1184762-67-1) + p-Anisaldehyde dimethyl acetal (2186-92-7) → (2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane (252342-44-2)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.200901740

upstream raw materials:

(Z)-(2R,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-4,6,8,10,12-pentamethyl-2-oxiranyltridec-8-en-3-ol

Downstream raw materials:

(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane

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