methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

Base Information

Chemical Name:methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate
CAS No.:160579-23-7
Molecular Formula:C₂₂H₂₈N₂O₈
Molecular Weight:448.473
Hs Code.:

Synonyms:methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

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Chemical Property of methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

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Technology Process of methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

There total 5 articles about methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate 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: 76.0%

: 89969-26-6
(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde

: 121056-95-9,89524-98-1
trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

: methyl (E,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

: 160579-23-7
methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

Guidance literature:: trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - -55 ℃; for 0.25h;

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde; In tetrahydrofuran; at -78 - -30 ℃;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

: 23632-67-9
(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

: 160579-23-7
methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / SOCl₂ / Heating

2.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

3.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

3.2: 76 percent / tetrahydrofuran / -78 - -30 °C

With thionyl chloride; potassium hexamethylsilazane; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; 3.2: Wittig-Horner reaction;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

: 115141-89-4
(4S)-3-(benzyloxycarbonyl)-4-(3-hydroxypropyl)-1,3-oxazolidin-5-one

: 160579-23-7
methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 20 - 40 °C

2.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

2.2: 76 percent / tetrahydrofuran / -78 - -30 °C

With potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.2: Wittig-Horner reaction;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8