benzyl N-[(3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate

Base Information

• Chemical Name: benzyl N-[(3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate
• CAS No.: 49705-98-8
• Molecular Formula: C12H16N2O4
• Molecular Weight: 252.27
• Hs Code.: 2924299090
• European Community (EC) Number: 256-436-9
• Mol file: 49705-98-8.mol

Synonyms:49705-98-8;C12H16N2O4;Cbz-L-threoninamide;N-Carbonyl-benzyloxy-L-threoninamide;AKOS025402076;AC-4332

Chemical Property of benzyl N-[(3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate

Chemical Property:

• Vapor Pressure: 2.07E-13mmHg at 25°C
• Melting Point: 103 - 106oC (Decomposes)
• Refractive Index: 1.58
• Boiling Point: 508.4 °C at 760 mmHg
• PKA: 10.96±0.46(Predicted)
• Flash Point: 261.3 °C
• PSA: 101.65000
• Density: 1.263 g/cm³
• LogP: 1.23870
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 252.11100700
• Heavy Atom Count: 18
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

N-BenzyloxycarbonylL-ThreonineAmide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of benzyl N-[(3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate

There total 6 articles about benzyl N-[(3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate 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%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-threonine amide hydrochloride (33209-01-7) → benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate (49705-98-8)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2021.108495

Reference yield:

N-benzyloxycarbonyl-L-treonine (19728-63-3) → benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate (49705-98-8)

Guidance literature:

With 4-methyl-morpholine; ammonia; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1021/ja00801a048

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate (49705-98-8)

Guidance literature:

With ammonia;

upstream raw materials:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

N-benzyloxycarbonyl-L-treonine

(2S,3R)-2-amino-3-hydroxybutanamide

benzyl chloroformate

Downstream raw materials:

(2S,3R)-2-amino-3-hydroxybutanamide

N-benzyloxycarbonyl-O-methanesulfonyl-L-threonine amide

(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt

L-threonine amide hydrochloride

Refernces

• 1、 -. "Ammonia curved the monocyclic parent nucleus method for the preparation of". Paragraph 0030; 0032; 0033. . Retrieved 2017/01/26.
• 2、 Okumura, Kazuo,Nakamura, Yutaka,Shin, Chung-Gi. "Total synthesis of a macrocyclic antibiotic, micrococcin P". . p. 1561 - 1569. Retrieved 2007/10/03.