(S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER

Base Information

• Chemical Name: (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER
• CAS No.: 82353-55-7
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.229
• Hs Code.: 2924299090
• Mol file: 82353-55-7.mol

Synonyms:Benzyl 1-methyl-2-oxoethylcarbamate;Propanal,2-[(benzyloxycarbonyl)amino];(S)-(1-formylpropan)-carbamic acid benzyl ester;(1-(S)-methyl-2-oxo-ethyl)carbamic acid benzyl ester;(S)-Benzyl (1-oxopropan-2-yl)carbamate;(S)-N-Cbz-alaninal;(S)-benzyl-(1-methyl-2-oxoethyl)carbamate;Cbz-L-alanine;Carbamic acid,(1-methyl-2-oxoethyl)-,phenylmethyl ester;(S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER;

Chemical Property of (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER

Chemical Property:

• PSA: 58.89000
• LogP: 1.70460

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Benzyloxycarbonyl-D-alaninal is an intermediate in the synthesis of (R)-1,1-Diethoxy-2-propanamine (D442115), which can be used for the synthesis of N-protected α-amino aldehydes occur as C-terminal units of peptide aldehydes with enzyme inhibitor activity, such as Leupeptin. They can also be used for the preparation of amino sugars, and unusual amino acids.

Technology Process of (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER

There total 24 articles about (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL 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: 100.0%

(S)-(-)-N-(benzyloxycarbonyl)alaninol (6429-44-3,61425-27-2,87905-97-3,66674-16-6) → benzyl (S)-1-oxopropan-2-ylcarbamate (82353-55-7,105499-10-3,141884-07-3,111955-03-4)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; Reflux;

DOI:10.1002/chem.201302732

Reference yield: 98.0%

(S)-2-benzyloxycarbonylamino-propionic acid methyl ester (28819-05-8) → benzyl (S)-1-oxopropan-2-ylcarbamate (82353-55-7,105499-10-3,141884-07-3,111955-03-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(97)00377-3

Reference yield: 95.0%

[(R)-2-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester (62023-24-9) → (R)-benzyl-(1-methyl-2-oxoethyl)carbamate (105499-10-3,111955-03-4,141884-07-3,82353-55-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -20 ℃;

DOI:10.1016/S0040-4039(00)86879-3

upstream raw materials:

(S)-2-benzyloxycarbonylamino-propionic acid methyl ester

(S)-(-)-N-(benzyloxycarbonyl)alaninol

(S)-benzyl (1-(N,O-dimethylhydroxylamine)-1-oxopropan-2-yl)carbamate

N-Cbz-Ala

Downstream raw materials:

(Z)-(S)-4-Benzyloxycarbonylamino-pent-2-enoic acid methyl ester

(2'R,3'S)-methyl 2-[3-(benzyloxycarbonylamino)-2-hydroxybutyl]propenoate

(2'S,3'S)-methyl 2-[3-(benzyloxycarbonylamino)-2-hydroxybutyl]propenoate

(2S,3SR)-2-{[(benzyloxy)carbonyl]amino}hex-5-en-3-ol

Refernces

• 1、 Garbacz, Mateusz,Stecko, Sebastian. "Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis". supporting information. p. 8578 - 8585. Retrieved 2021/10/20.
• 2、 -. "DIHYDROOROTATE DEHYDROGENASE INHIBITORS". Page/Page column 98. . Retrieved 2020/08/22.