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

Base Information

Chemical Name:(2R,3S,5S,6R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexan-3-ol
CAS No.:170707-48-9
Molecular Formula:C₂₉H₄₅NO₈Si
Molecular Weight:563.764
Hs Code.:

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

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

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

There total 4 articles about (2R,3S,5S,6R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 170901-52-7
(2R,3S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexane-1,3-diol

: 170707-48-9
(2R,3S,5S,6R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexan-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1021/ja00147a027

Reference yield:

: 134333-50-9
2,5-dimethoxy-3-nitrobenzaldehyde dimethyl acetal

: 170707-48-9
(2R,3S,5S,6R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / TMSOTf / CH₂Cl₂ / 16 h / -78 °C

2: 1.) BH₃*SMe₂, 2.) 5M aq. NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, 18 h, 2.) THF, from 0 deg C to RT, 120 min

3: imidazole / diethyl ether; dimethylformamide / 0 °C

With 1H-imidazole; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; dihydrogen peroxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja974318b

Reference yield:

: (2R,3R,E)-methyl 2-(benzyloxy)-3-(dimethyl(phenyl)silyl)hex-4-enoate

: 170707-48-9
(2R,3S,5S,6R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / TMSOTf / CH₂Cl₂ / 16 h / -78 °C

2: 1.) BH₃*SMe₂, 2.) 5M aq. NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, 18 h, 2.) THF, from 0 deg C to RT, 120 min

3: imidazole / diethyl ether; dimethylformamide / 0 °C

With 1H-imidazole; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; dihydrogen peroxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja974318b