(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

Base Information

Chemical Name:(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol
CAS No.:1378532-01-4
Molecular Formula:C₄₇H₆₀O₅SSi₂
Molecular Weight:793.227
Hs Code.:

Synonyms:(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

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Chemical Property of (2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

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Technology Process of (2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

There total 4 articles about (2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-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: 90.0%

: 1378532-00-3
(3S,4S)-3-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)-3-(methylthio)pentane-1,4-diol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1378532-01-4
(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Inert atmosphere;

Reference yield:

: 40587-54-0,106692-64-2
α-methylthio-γ-butyrolactone

: 1378532-01-4
(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: silver(I) hexafluorophosphate; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / -20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

3: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; silver(I) hexafluorophosphate; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: asymmetric aldol reaction;
DOI:10.1002/anie.201200520

Reference yield:

: 121289-23-4
p-methoxybenzyloxyacetaldehyde

: 1378532-01-4
(2S,3S)-5-((tert-butyldiphenylsilyl)oxy)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1-((4-methoxybenzyl)oxy)-3-(methylthio)pentan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: silver(I) hexafluorophosphate; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / -20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

3: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; silver(I) hexafluorophosphate; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: asymmetric aldol reaction;
DOI:10.1002/anie.201200520