(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

Base Information

Chemical Name:(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol
CAS No.:869732-24-1
Molecular Formula:C₃₄H₄₇BrO₅Si
Molecular Weight:643.734
Hs Code.:

Synonyms:(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

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Chemical Property of (2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

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Technology Process of (2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

There total 8 articles about (2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-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: 97.0%

: 869732-15-0
(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 869732-24-1
(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

Guidance literature:: With 1H-imidazole; In diethyl ether; N,N-dimethyl-formamide; at 0 ℃; for 4h;
DOI:10.1021/ja055384d

Reference yield:

: 869732-13-8
3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde

: 869732-24-1
(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

2.1: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

3.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

3.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

4.1: 97 percent / 1H-imidazole / dimethylformamide; diethyl ether / 4 h / 0 °C

With 1H-imidazole; triethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja055384d

Reference yield:

: 869732-23-0
(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

: 869732-24-1
(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

1.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

2.1: 97 percent / 1H-imidazole / dimethylformamide; diethyl ether / 4 h / 0 °C

With 1H-imidazole; dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja055384d