tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

Base Information

Chemical Name:tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate
CAS No.:1291083-49-2
Molecular Formula:C₂₂H₃₉NO₄Si
Molecular Weight:409.641
Hs Code.:

Synonyms:tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

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Chemical Property of tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

There total 4 articles about tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate 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:

: 1291083-48-1
(R)-(-)-tert-butyl 5-(tert-butyldimethylsilyloxy)-2-oxo-1-phenylpentylcarbamate

: tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

: 1291083-49-2
tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In ethanol; dichloromethane; at -78 - -40 ℃; for 7h; optical yield given as %de; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.02.031

Reference yield:

: 1-(tert-butyldimethylsilyloxy)-4-nitrobutane

: tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

: 1291083-49-2
tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1: cesiumhydroxide monohydrate; N-benzyl quinidinium chloride / toluene / 40 h / -55 °C / Inert atmosphere

2: sodium nitrite / water; N,N-dimethyl-formamide / 12 h / 45 °C / Inert atmosphere

3: sodium tetrahydroborate; cerium(III) chloride heptahydrate / ethanol; dichloromethane / 7 h / -78 - -40 °C / Inert atmosphere

With sodium tetrahydroborate; N-benzyl quinidinium chloride; cesiumhydroxide monohydrate; cerium(III) chloride heptahydrate; sodium nitrite; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: aza-Henry reaction;
DOI:10.1016/j.tet.2011.02.031

Reference yield:

: tert-butyl 5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate

: tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

: 1291083-49-2
tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpentylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium nitrite / water; N,N-dimethyl-formamide / 12 h / 45 °C / Inert atmosphere

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / ethanol; dichloromethane / 7 h / -78 - -40 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium nitrite; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.02.031