(2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

Base Information

• Chemical Name: (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol
• CAS No.: 252006-18-1
• Molecular Formula: C₆₀H₈₆O₇Si₃
• Molecular Weight: 1003.6

Synonyms:(2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

Chemical Property of (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

Chemical Property:

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Safty Information:

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Technology Process of (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

There total 21 articles about (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-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: 26.0%

(2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one (240821-06-1) → (2R,3E,5S,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol (240821-12-9) + (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol (252006-18-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -50 - -30 ℃; for 0.333333h;

DOI:10.1248/cpb.47.1288

Reference yield:

(2E,4R)-5-(tert-butyldiphenylsilyloxy)-2-iodo-4-methyl-2-pentene (240821-04-9) + (2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal (240820-99-9) → (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol (252006-18-1) + (2R,3E,5R,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

Guidance literature:

(2E,4R)-5-(tert-butyldiphenylsilyloxy)-2-iodo-4-methyl-2-pentene; With n-butyllithium; In diethyl ether; pentane; at -78 - 20 ℃; for 2h;

(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal; In diethyl ether; at -78 - -30 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1248/cpb.47.1288

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (2R,3E,5S,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol (252006-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / Ph₃P / CH₂Cl₂ / -60 °C

2.1: 96 percent / n-BuLi / hexane; tetrahydrofuran / 20 °C

3.1: 50 percent / Cp₂ZrHCl; I₂ / benzene / 45 °C

4.1: n-BuLi / pentane; diethyl ether / 2 h / -78 - 20 °C

4.2: diethyl ether / 4 h / -78 - -30 °C

With Schwartz's reagent; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; benzene; 1.1: Substitution / 2.1: Methylation / 3.1: Substitution / 4.1: Metallation / 4.2: Condensation;

DOI:10.1248/cpb.47.1288

upstream raw materials:

(2E,4R)-5-(tert-butyldiphenylsilyloxy)-2-iodo-4-methyl-2-pentene

(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

(2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

Downstream raw materials:

2,2-Dimethyl-propionic acid (E)-(2R,3S,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(1S,2R)-3-(tert-butyl-diphenyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-2-methyl-propyl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester

(2S,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-3-(3,4-dimethoxybenzyloxy)-5-methoxymethoxy-2,6,8-trimethyl-6,9-undecadienal

Acetic acid (E)-(1S,4R)-1-[(1S,2S,3R)-1-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-3-methyl-butyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl ester

(2Z,4S,5E,7S,8S,9S,10R)-8-(tert-butyldimethylsilyloxymethyl)-9,11-[(S)-3,4-dimethoxybenzylidenedioxy]-7-methoxymethyl-4,6,10-trimethyl-2,5-undecadiene

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