(3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol

Base Information

• Chemical Name: (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol
• CAS No.: 184291-37-0
• Molecular Formula: C₂₂H₄₀O₄Si
• Molecular Weight: 396.643

Synonyms:(3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol

Chemical Property of (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol

Chemical Property:

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Technology Process of (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol

There total 4 articles about (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-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:

p-Methoxybenzyl bromide (2746-25-0) → (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol (184291-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaH

2: 1.) O₃, 2.) Me₂S

With dimethylsulfide; sodium hydride; ozone;

DOI:10.1021/ja961374o

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol (184291-37-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 48percent aq. HBr / 0.5 h / Ambient temperature

2: 90 percent / NaH

3: 1.) O₃, 2.) Me₂S

With dimethylsulfide; hydrogen bromide; sodium hydride; ozone;

DOI:10.1021/ja961374o

Reference yield:

tert-Butyl-[(2S,3R,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-enyloxy]-dimethyl-silane (184488-77-5) → (3S,4S,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-ol (184291-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S

With dimethylsulfide; ozone;

DOI:10.1021/ja961374o

upstream raw materials:

methylmagnesium bromide

(2R,3S,4S)-5-(tert-butyldimethylsiloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

p-Methoxybenzyl bromide

4-Methoxybenzyl alcohol

Downstream raw materials:

2,2-dimethylpropanoic acid, [2S-(2α(5E,7Z,9S,10S,11R,13R,15Z,17R,18R,20Z,22R),3β,4β,5α,6β)]-18,20-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-23-(4-{[(1,1-dimethylethyl)dimethylsilyl]oxy}tetrahydro-3,5-dimethyl-6-(phenylthio)-2H-pyran-2-yl)-9,11,13,

C₇₂H₁₂₂O₉SSi₃

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