(2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester

Base Information

Chemical Name:(2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester
CAS No.:149287-46-7
Molecular Formula:C₁₅H₁₉NO₅
Molecular Weight:293.32
Hs Code.:
DSSTox Substance ID:DTXSID101125363
Nikkaji Number:J544.296F,J544.297D

Synonyms:DTXSID101125363;(2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester;(2Z,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester;2-Pentenoic acid, 2-[(methoxycarbonyl)amino]-4-(phenylmethoxy)-, methyl ester, [S-(Z)]-;149287-46-7

Suppliers and Price of (2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester

Chemical Property:

XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:293.12632271
Heavy Atom Count:21
Complexity:374

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(C=C(C(=O)OC)NC(=O)OC)OCC1=CC=CC=C1
Isomeric SMILES:C[C@@H](/C=C(/C(=O)OC)\NC(=O)OC)OCC1=CC=CC=C1

Technology Process of (2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester

There total 5 articles about (2E,4S)-2-(Methoxycarbonylamino)-4-(benzyloxy)-2-pentenoic acid methyl ester 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: 77.0%

: 81445-44-5
(S)-2-(benzyloxy)propanal

: 144001-86-5
Methyl 2-(dimethoxyphosphinyl)-2-ethanoate

: 149287-46-7
(4S)-Methyl 4-(benzyloxy)-2--(2Z)-pentenoate

Guidance literature:: With potassium tert-butylate; In dichloromethane;
DOI:10.1021/jo00068a047

Reference yield:

: 143995-55-5
2--2-methoxyethanoate

: 149287-46-7
(4S)-Methyl 4-(benzyloxy)-2--(2Z)-pentenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 1) phosphorus trichloride / 1) toluene, 70 deg C, 18 h, 2) 2 h, 70 deg C

2: iPr₂NLi / tetrahydrofuran / 2 h / -78 to 24 deg C

With lithium diisopropyl amide; phosphorus trichloride; In tetrahydrofuran;
DOI:10.1021/jo00068a047

Reference yield:

: 100-39-0
benzyl bromide

: 149287-46-7
(4S)-Methyl 4-(benzyloxy)-2--(2Z)-pentenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 1) NaH, 2) nBu₄NI / 1) THF, 0 deg C, 15 min, 2) 0 to 24 deg C, 30 min

2: 97 percent / iBu₂AlH / hexane; diethyl ether / -78 °C

3: iPr₂NLi / tetrahydrofuran / 2 h / -78 to 24 deg C

With tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jo00068a047