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

Base Information

Chemical Name:(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tertbutyldiphenylsilyl)oxy]-1-hexene
CAS No.:1385033-96-4
Molecular Formula:C₃₅H₅₀O₄Si₂
Molecular Weight:590.951
Hs Code.:

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

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

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

There total 4 articles about (4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tertbutyldiphenylsilyl)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: 92.0%

: 1385033-94-2
(2S,3R)-1-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)-5-trimethylsilylmethyl-5-hexen-3-ol

: 420-37-1
trimethoxonium tetrafluoroborate

: 1385033-96-4
(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tertbutyldiphenylsilyl)oxy]-1-hexene

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at 22 ℃; Inert atmosphere; Molecular sieve; Cooling with ice;
DOI:10.1021/ol3015682

Reference yield:

: 870119-18-9
(2S)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal

: 1385033-96-4
(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tertbutyldiphenylsilyl)oxy]-1-hexene

Guidance literature:: Multi-step reaction with 2 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 / 22 °C / Inert atmosphere; Molecular sieve; Cooling with ice

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;
DOI:10.1021/ol3015682

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1385033-96-4
(4R,5S)-2-trimethylsilylmethyl-4-methoxy-5-(4-methoxybenzyloxy)-6-[(tertbutyldiphenylsilyl)oxy]-1-hexene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane

2.1: methylenedimethyl sulfurane / tetrahydrofuran / -10 °C

3.1: 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

3.2: 2 h / -78 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 22 °C / Inert atmosphere; Molecular sieve; Cooling with ice

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; methylenedimethyl sulfurane; (4R,5R)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol3015682