(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

Base Information

Chemical Name:(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane
CAS No.:1372138-79-8
Molecular Formula:C₂₈H₃₈N₂O₆
Molecular Weight:498.62
Hs Code.:

Synonyms:(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

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Chemical Property of (2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

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Technology Process of (2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

There total 3 articles about (2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane 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: 51.0%

: 1372138-78-7
(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenylnon-4-ene

: 1372138-79-8
(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1021/jm3001136

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 1372138-79-8
(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - -30 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 16 h / 25 °C

3.1: lithium tri-t-butoxyaluminum hydride / ethanol / -78 - -60 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jm3001136

Reference yield:

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

: 1372138-79-8
(2S,3S,4R,5R)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenylnonane

Guidance literature:: Multi-step reaction with 3 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 16 h / 25 °C

2: lithium tri-t-butoxyaluminum hydride / ethanol / -78 - -60 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jm3001136