ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

Base Information

Chemical Name:ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate
CAS No.:1355026-76-4
Molecular Formula:C₂₂H₃₃NO₅
Molecular Weight:391.508
Hs Code.:

Synonyms:ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

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Chemical Property of ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

Chemical Property:

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Technology Process of ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

There total 3 articles about ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate 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:

: C₂₂H₃₁NO₅

: 1355026-76-4
ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

Guidance literature:: With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 20 ℃; for 1.08333h; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 494224-49-6
(R)-ethyl 4-(tert-butoxycarbonylamino)-5-oxopentanoate

: 1355026-76-4
ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C

2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

With borane-THF; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; mineral oil; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 597577-78-1
(4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester

: 1355026-76-4
ethyl (4R,5E,7S)-8-(3-methylphenyl)-7-hydroxy-4-({tert-butyloxycarbonyl}amino)-5-octenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -70 - -40 °C

1.2: 0.5 h / -40 - -5 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

With borane-THF; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018