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

Base Information

• Chemical Name: (4S,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene
• CAS No.: 1385033-79-3
• Molecular Formula: C₂₅H₄₆O₄Si₂
• Molecular Weight: 466.809
• Mol file: 1385033-79-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (4S,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene 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) → (4S,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene (1385033-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine / dichloromethane / 16 h / 22 °C / Inert atmosphere

1.2: 4 h / -78 °C / Inert atmosphere

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

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

DOI:10.1021/ol3015682

Reference yield: 89.0%

(4S,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene (1385033-79-3) + (2R)-2-methoxymethoxy-3-phenylacetaldehyde (107536-09-4,120113-93-1,121842-15-7,121842-14-6) → (1R,2R)-1-(methoxymethoxy)-1-phenyl-4-[(2S,3S)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-3-methoxy]butyl-4-penten-2-ol (1385034-10-5)

Guidance literature:

(2R)-2-methoxymethoxy-3-phenylacetaldehyde; With magnesium bromide ethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

(4S,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: 87.0%

(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal (866454-44-6) + (4S,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tert-butyldimethylsilyl)oxy]-1-hexene (1385033-79-3) → (2R,3R,7S,8S)-1-[(tert-butyldiphenylsilyl)oxy]-2,8-bis(4-methoxybenzyloxy)-5-methylene-7-methoxy-9-[(tert-butyldimethylsilyl)oxy]-3-nonanol (1385034-08-1)

Guidance literature:

(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal; With magnesium bromide ethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

(4S,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

upstream raw materials:

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

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

Downstream raw materials:

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

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

(1R,2R)-1-(methoxymethoxy)-1-phenyl-4-[(2S,3S)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-3-methoxy]butyl-4-penten-2-ol