(2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol

Base Information

• Chemical Name: (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol
• CAS No.: 1385034-03-6
• Molecular Formula: C₃₉H₆₆O₈Si₂
• Molecular Weight: 719.119

Synonyms:(2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol

Chemical Property of (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol

Chemical Property:

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Technology Process of (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol

There total 3 articles about (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol 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: 80.0%

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal (180153-95-1) + (4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene (1385033-80-6) → (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol (1385034-03-6)

Guidance literature:

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal; With magnesium bromide ethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene; In dichloromethane; at -78 - -26 ℃; for 13h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol3015682

Reference yield:

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal (180153-95-1) → (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol (1385034-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; (4R,5R)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine / dichloromethane / 16 h / 0 - 22 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 13 h / 22 °C / Molecular sieve; Inert atmosphere

3.1: magnesium bromide ethyl etherate / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

3.2: 13 h / -78 - -26 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methylpyridine; (4R,5R)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine; magnesium bromide ethyl etherate; In dichloromethane;

DOI:10.1021/ol3015682

Reference yield:

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol (1385033-81-7) → (2S,3S,7R,8S)-1,9-bis-(tert-butyldimethylsilyloxy)-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-3-nonanol (1385034-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 13 h / 22 °C / Molecular sieve; Inert atmosphere

2.1: magnesium bromide ethyl etherate / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

2.2: 13 h / -78 - -26 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methylpyridine; magnesium bromide ethyl etherate; In dichloromethane;

DOI:10.1021/ol3015682

upstream raw materials:

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal

(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol

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