(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

Base Information

Chemical Name:(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane
CAS No.:198208-15-0
Molecular Formula:C₂₃H₂₉NO₄
Molecular Weight:383.488
Hs Code.:

Synonyms:(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

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Chemical Property of (2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

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Technology Process of (2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

There total 4 articles about (2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane 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: 70.0%

: 198208-08-1
(4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-1,6-diphenyl-2-hexene

: 198208-15-0
(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Ambient temperature;
DOI:10.1021/jo971202p

Reference yield:

: 51987-73-6
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

: 198208-15-0
(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / n-BuLi / tetrahydrofuran

2: 50 percent / K₂CO₃ / ethanol

3: NaBH₄ / methanol / 0 °C

4: 70 percent / m-CPBA / CH₂Cl₂

With sodium tetrahydroborate; n-butyllithium; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2: Horner-Emmons olefination;
DOI:10.1016/j.bmc.2003.08.004

Reference yield:

: 176504-90-8
dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate

: 198208-15-0
(2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / K₂CO₃ / ethanol

2: NaBH₄ / methanol / 0 °C

3: 70 percent / m-CPBA / CH₂Cl₂

With sodium tetrahydroborate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; 1: Horner-Emmons olefination;
DOI:10.1016/j.bmc.2003.08.004