(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid

Base Information

• Chemical Name: (S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid
• CAS No.: 23632-66-8
• Molecular Formula: C13H13 N O6
• Molecular Weight: 279.249
• DSSTox Substance ID: DTXSID701173910
• Nikkaji Number: J698.151H
• Mol file: 23632-66-8.mol

Synonyms:23632-66-8;(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid;(S)-2-(3-((Benzyloxy)carbonyl)-5-oxooxazolidin-4-yl)acetic acid;2-[(4S)-5-oxo-3-phenylmethoxycarbonyl-1,3-oxazolidin-4-yl]acetic acid;(S)-(+)-3-(Benzyloxyxarbonyl)-5-ox-4-oxazolidineacetic Acid;SCHEMBL346937;DTXSID701173910;(S)-2-(3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl)acetic acid;YAA63266;AKOS015889477;A816815;3-(Benzyloxycarbonyl)-5-oxooxazolidine-4beta-acetic acid;(4S)-5-Oxo-3-[(phenylmethoxy)carbonyl]-4-oxazolidineacetic acid;(S)-2-(3-((Benzyloxy)carbonyl)-5-oxooxazolidin-4-yl)aceticacid;(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid, 97%

Chemical Property of (S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid

Chemical Property:

• Vapor Pressure: 3.53E-13mmHg at 25°C
• Melting Point: 84-87 ºC
• Boiling Point: 555.6°Cat760mmHg
• PKA: 4.17±0.10(Predicted)
• Flash Point: 289.8°C
• PSA: 93.14000
• Density: 1.411g/cm³
• LogP: 0.92070
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 279.07428713
• Heavy Atom Count: 20
• Complexity: 390

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(+)-3-(Benzyloxyxarbonyl)-5-ox-4-oxazolidineaceticAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1N(C(C(=O)O1)CC(=O)O)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1N([C@H](C(=O)O1)CC(=O)O)C(=O)OCC2=CC=CC=C2
• Uses: (S)-(+)-3-(Benzyloxyxarbonyl)-5-ox-4-oxazolidineacetic Acid is used in the preparation of Tryprostatin A and B. Also used in the synthesis of cyclic lactam analogs of α-melanotropin.

Technology Process of (S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid

There total 3 articles about (S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidineacetic acid 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: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-Cbz-L-Asp (1152-61-0) → (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1h; Heating;

DOI:10.1055/s-1989-27311

Reference yield: 95.0%

N-Cbz-L-Asp (1152-61-0) → (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 1.66667h; Heating;

DOI:10.1016/S0040-4020(01)88118-7

Reference yield: 91.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-benzyloxycarbonyl-L-aspartic acid (67809-70-5) → (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; for 2h; Heating;

upstream raw materials:

formaldehyd

N-Cbz-L-Asp

N-benzyloxycarbonyl-L-aspartic acid

Downstream raw materials:

(S)-4-(9H-Fluoren-9-ylmethoxycarbonylmethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

phenylmethyl (4S)-5-oxo-4-{2-oxo-2-[(phenylmethyl)oxy]ethyl}-1,3-oxazolidine-3-carboxylate

(4S)-N-Benzyloxycarbonyl₄-methoxycarbonylmethyl-1,3-oxazolidin-5-one

C₂₇H₃₃N₃O₁₄

Refernces

• 1、 Uma,Lalithamba,Chandramohan,Lingaraju. "A Facile Synthesis of Hydroxamic Acids of Nα-Protected Amino Acids Employing BDMS, a Study of Their Molecular Docking and Their Antibacterial Activities". . p. 161 - 174. Retrieved 2019/04/27.
• 2、 Chandan, Nandkishkor,Moloney, Mark G.. "A direct route to 2,2,5-trisubstituted pyrrolidines of relevance to kaitocephalin". supporting information. p. 1987 - 1990. Retrieved 2013/04/10.