(2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

Base Information

• Chemical Name: (2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
• CAS No.: 100157-53-7
• Molecular Formula: C13H17NO5
• Molecular Weight: 267.27778
• DSSTox Substance ID: DTXSID00426302
• Wikidata: Q82239244
• Mol file: 100157-53-7.mol

Synonyms:100157-53-7;(2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate;N-Cbz-D-allo-threonine Methyl Ester;methyl (2R,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate;D-Allothreonine, N-[(phenylmethoxy)carbonyl]-, methyl ester;Methyl N-[(benzyloxy)carbonyl]-D-allothreoninate;METHYL (2R,3R)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-HYDROXYBUTANOATE;(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate;MFCD22416539;DTXSID00426302;(2R,3R)-Methyl2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate;AKOS015998802;AS-32463;EN300-7407214;A897567;N-CbZ-D-allo-threonine methyl ester (CbZ-D-aThr-OMe);98777-33-4

Chemical Property of (2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 267.11067264
• Heavy Atom Count: 19
• Complexity: 301

Purity/Quality:

98.5% ^*data from raw suppliers

(2R,3R)-Methyl2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

There total 9 articles about (2R,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 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: 98.0%

(2R,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (60538-18-3) + benzyl chloroformate (501-53-1,94274-21-2) → N-carbobenzyloxy-D-allo-threonine methyl ester (100157-53-7)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃; for 12h;

DOI:10.1002/jlac.198519851117

Reference yield:

(+/-) threonine methyl ester hydrochloride (39994-75-7,60538-15-0,60538-18-3,62076-66-8,76419-75-5,79617-27-9,108724-12-5) + benzyl chloroformate (501-53-1,94274-21-2) → Z-DL-Thr-OMe (57224-63-2,62076-80-6,84449-06-9,98777-33-4,98777-34-5,100157-53-7)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1021/jo00433a015

Reference yield:

H-DL-aThr-OMe*HCl (39994-75-7,60538-15-0,60538-18-3,62076-66-8,76419-75-5,79617-27-9,108724-12-5) + benzyl chloroformate (501-53-1,94274-21-2) → Z-DL-aThr-OMe (57224-63-2,62076-80-6,84449-06-9,98777-33-4,98777-34-5,100157-53-7)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃; for 12h;

DOI:10.1002/jlac.198519851117

upstream raw materials:

(2R,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride

benzyl chloroformate

methanol

(2S,5S,6R)-6-Methyl-5-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-2-((R)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-4-one

Downstream raw materials:

((3R,5R)-5-Methyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

((3R,5S)-5-Methyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester

[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester

Refernces

• 1、 Golebiowski, A.,Jurczak, J.. "HIGH-PRESSURE CYCLOADDITION OF 1-METHOXY-1,3-BUTADIENE TO N,O-PROTECTED D-THREONINALS AND D-ALLO-THREONINALS". . p. 1037 - 1044. Retrieved 2007/10/02.
• 2、 Aydin,Lucht,Konig,et al.. "Structure elucidation of the peptide antibiotics herbicolin A and B". . p. 2285 - 2300. Retrieved 2007/10/02.