Z-D-Met-OH

Base Information

• Chemical Name: Z-D-Met-OH
• CAS No.: 28862-80-8
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.348
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID501316639
• Nikkaji Number: J208.195D
• Mol file: 28862-80-8.mol

Synonyms:Z-D-Met-OH;28862-80-8;Cbz-D-Methionine;N-Cbz-D-methionine;N-Carbobenzoxy-D-methionine;Z-D-METHIONINE;(R)-2-(((Benzyloxy)carbonyl)amino)-4-(methylthio)butanoic acid;(2R)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoic acid;MFCD00026043;SCHEMBL4169134;CARBOBENZYLOXY-D-METHIONINE;DTXSID501316639;AKOS016843667;AM81983;CS-W010036;DS-5113;HY-W009320;N- alpha -Benzyloxycarbonyl-D-methionine;D-Methionine, N-[(phenylmethoxy)carbonyl]-;F10832;EN300-6747558;N-BenZyloxycarbonyl-D-methionine, 98% (CbZ-D-Met-OH);(R)-2-(benzyloxycarbonylamino)-4-(methylthio)butanoic acid;(2R)-2-{[(benzyloxy)carbonyl]amino}-4-(methylsulfanyl)butanoic acid

Chemical Property of Z-D-Met-OH

Chemical Property:

• Vapor Pressure: 5.22E-11mmHg at 25°C
• Melting Point: 67-69 °C
• Refractive Index: 26 ° (C=1, MeOH)
• Boiling Point: 504.7 °C at 760 mmHg
• Flash Point: 259 °C
• PSA: 100.93000
• Density: 1.253 g/cm³
• LogP: 2.51000
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 283.08782920
• Heavy Atom Count: 19
• Complexity: 292

Purity/Quality:

min 98.0% ^*data from raw suppliers

Z-D-methionine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CSCC[C@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: N-Cbz-D-methionine is an N-Cbz-protected form of D-Methionine (M260550). D-Methionine is an isomer of L-Methionine (M260440), and is known to be a cytoprotectant against Cisplatin (C499500), an anticancer agent. D-Methionine is also used to prevent noise- and drug-induced hearing loss, as well as hair loss (all of which may also be caused by Cisplatin or aminoglycosides).

Technology Process of Z-D-Met-OH

There total 10 articles about Z-D-Met-OH 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: 87.0%

D-methionine (348-67-4,26062-47-5,58576-49-1) + benzyl chloroformate (501-53-1,94274-21-2) → (2R)-2-[[(benzyloxy)carbonyl]amino]-4-(methylsulfanyl)butanoic acid (1152-62-1,4434-61-1,28862-80-8)

Guidance literature:

With sodium hydrogencarbonate; at 23 ℃; for 24h;

DOI:10.1021/jf00058a034

Reference yield: 84.0%

ethanol (64-17-5) + N-(benzyloxycarbonyl)methionine (4434-61-1) → (2R)-2-[[(benzyloxy)carbonyl]amino]-4-(methylsulfanyl)butanoic acid (1152-62-1,4434-61-1,28862-80-8) + L-Z-Met-OEt (113718-97-1)

Guidance literature:

industrial papain; at 50 ℃; for 4h; pH 4,5 (citrate buffer, cystein*HCl);

DOI:10.1016/0223-5234(87)90273-X

Reference yield:

DL-Met/PyS + benzyl chloroformate (501-53-1,94274-21-2) → Cbz-Met-OH (1152-62-1) + (2R)-2-[[(benzyloxy)carbonyl]amino]-4-(methylsulfanyl)butanoic acid (1152-62-1,4434-61-1,28862-80-8)

Guidance literature:

DL-Met/PyS; With alpha cyclodextrin; In ethanol; dimethyl sulfoxide; at 50 ℃; for 24h;

benzyl chloroformate;

DOI:10.1016/j.tet.2020.131100

upstream raw materials:

N-(benzyloxycarbonyl)methionine

aniline

ethanol

D-methionine

Downstream raw materials:

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

(2S)-2-but-3-en-1-ol

D-2-<(benzyloxycarbonyl)amino>-4-butyrolactone

C₁₈H₂₅NO₆S

Refernces

• 1、 Hattori, Tetsutaro,Kitamoto, Yuichi,Maeda, Tetsuya,Miyoshi, Ikuko,Morohashi, Naoya. "Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin". . . Retrieved 2020/04/01.
• 2、 Wolfe, Saul,Wilson, Marie-Claire,Cheng, Ming-Huei,Shustov, Gennady V.,Akuche, Christiana I.. "Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones". . p. 937 - 960. Retrieved 2007/10/03.