(R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

Base Information

• Chemical Name: (R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate
• CAS No.: 98854-91-2
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40508737
• Wikidata: Q82365884
• Mol file: 98854-91-2.mol

Synonyms:98854-91-2;(R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate;Z-D-Alpha-vinyl-gly-ome;methyl (2R)-2-(phenylmethoxycarbonylamino)but-3-enoate;methyl (R)-2-(((benzyloxy)carbonyl)amino)but-3-enoate;Methyl (2R)-2-{[(benzyloxy)carbonyl]amino}but-3-enoate;(R)-Methyl2-(((benzyloxy)carbonyl)amino)but-3-enoate;SCHEMBL22747610;DTXSID40508737;AMY21449;FD6052;MFCD16038247;AKOS015850854;AS-49276;(R)-Methyl 2-(((benZyloxy)carbonyl)amino)but-3-enoate (CbZ-D-Gly(Vinyl)-OMe)

Chemical Property of (R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

Chemical Property:

• PSA: 68.12000
• LogP: 1.84480
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-Methyl2-(((benzyloxy)carbonyl)amino)but-3-enoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C=C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: COC(=O)[C@@H](C=C)NC(=O)OCC1=CC=CC=C1

Technology Process of (R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

There total 7 articles about (R)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate 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: 55.0%

(R)-2-Benzyloxycarbonylamino-4-methanesulfinyl-butyric acid methyl ester → N-<(benzyloxy)carbonyl>-D-vinylglycine methyl ester (98854-91-2)

Guidance literature:

at 150 ℃; for 2h; under 0.5 Torr;

DOI:10.1039/b212270g

Reference yield:

D-methionine methyl ester (21691-49-6,874219-77-9) → N-<(benzyloxy)carbonyl>-D-vinylglycine methyl ester (98854-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / aq. K₂CO₃ / ethyl acetate / 2 h / 0 - 20 °C

2: 82 percent / NaIO₄ / aq. methanol / 2 h / 0 °C

3: 55 percent / 2 h / 150 °C / 0.5 Torr

With sodium periodate; potassium carbonate; In methanol; ethyl acetate;

DOI:10.1039/b212270g

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-<(benzyloxy)carbonyl>-D-vinylglycine methyl ester (98854-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / aq. K₂CO₃ / ethyl acetate / 2 h / 0 - 20 °C

2: 82 percent / NaIO₄ / aq. methanol / 2 h / 0 °C

3: 55 percent / 2 h / 150 °C / 0.5 Torr

With sodium periodate; potassium carbonate; In methanol; ethyl acetate;

DOI:10.1039/b212270g

upstream raw materials:

D-Glutamic acid

N-<(benzoyloxy)carbonyl>-D,L-vinylglycine methyl ester

D-methionine methyl ester

benzyl chloroformate

Downstream raw materials:

methyl (2R,3R)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate

(R)-(1-hydroxymethallyl)carbamic acid benzyl ester

C₁₉H₂₀ClNO₅Se

(S)-2-Benzyloxycarbonylamino-3-chloro-but-3-enoic acid methyl ester

Refernces

• 1、 Huwe, Christoph M.,Blechert, Siegfried. "A flexible synthesis of azasugars and homoazasugars via olefin metathesis". . p. 61 - 67. Retrieved 2007/10/03.