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

Base Information

• Chemical Name: (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol
• CAS No.: 1385033-81-7
• Molecular Formula: C₂₄H₄₄O₄Si₂
• Molecular Weight: 452.782
• Mol file: 1385033-81-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-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:

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal (180153-95-1) + 1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene (164662-96-8) → (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol (1385033-81-7)

Guidance literature:

1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene; 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; In dichloromethane; at 0 - 22 ℃; for 16h; Inert atmosphere;

(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal; In dichloromethane; at -78 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol3015682

Reference yield: 87.0%

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol (1385033-81-7) + trimethoxonium tetrafluoroborate (420-37-1) → (4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene (1385033-80-6)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at 22 ℃; for 13h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol3015682

Reference yield:

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol (1385033-81-7) → (2R,3R,7R,8S)-1-[(tert-butyldiphenylsilyl)oxy]-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-9-[(tert-butyldimethylsilyl)oxy]-3-nonanol (1385034-04-7)

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

1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene

Downstream raw materials:

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

(2R,3R,7R,8S)-1-[(tert-butyldiphenylsilyl)oxy]-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-9-[(tert-butyldimethylsilyl)oxy]-3-nonanol

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