Z-Oxylysine

Base Information

• Chemical Name: Z-Oxylysine
• CAS No.: 59221-35-1
• Molecular Formula: C14H19 N O5
• Molecular Weight: 281.309
• DSSTox Substance ID: DTXSID70207968
• Nikkaji Number: J1.375.762C
• Wikidata: Q83082006
• Mol file: 59221-35-1.mol

Synonyms:(N-(6)-benzyloxycarbonyl)-2-hydroxylysine;(R)-isomer of Z-oxylysine;N(epsilon) CBZ-L-oxylysine;N(epsilon)-carbobenzoxyoxylysine;Z-oxylysine

Chemical Property of Z-Oxylysine

Chemical Property:

• Vapor Pressure: 1.05E-11mmHg at 25°C
• Boiling Point: 521.5°C at 760 mmHg
• Flash Point: 269.2°C
• PSA: 99.35000
• Density: 1.244g/cm³
• LogP: 1.73300
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 281.12632271
• Heavy Atom Count: 20
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCCCC(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NCCCC[C@@H](C(=O)O)O

Technology Process of Z-Oxylysine

There total 8 articles about Z-Oxylysine 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: 95.0%

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → (S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid (59221-35-1)

Guidance literature:

With sodium nitrite; In water; at 0 ℃; for 0.333333h;

DOI:10.1021/jo0006573

Reference yield: 94.0%

(S)-6-Amino-2-hydroxyhexanoic acid (42491-84-9) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid (59221-35-1)

Guidance literature:

With sodium hydroxide; at 0 ℃; for 45h; pH 10;

DOI:10.1021/jm00396a033

Reference yield:

ethyl acetate n-hexane + (S)-6-Amino-2-hydroxyhexanoic acid (42491-84-9) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-6-[[(Phenylmethoxy)carbonyl]amino]-2-hydroxyhexanoic acid (59221-35-1)

Guidance literature:

In sodium hydroxide;

upstream raw materials:

(S)-6-Amino-2-hydroxyhexanoic acid

benzyl chloroformate

6-benzyloxycarbonylamino-2-oxo-hexanoic acid

N₆-[(benzyloxy)carbonyl]-L-lysine

Downstream raw materials:

(2S,3aS,7aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-indole-2-carboxylic acid ethyl ester

(2S,3aS,6aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

<1(R^*),2α,4α>-4-cyclohexyl-1-<2-hydroxy-1-oxo-6-<<(phenylmethoxy)carbonyl>amino>hexyl>-L-proline phenylmethyl ester

(2S,4S)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-4-cyclohexyl-pyrrolidine-2-carboxylic acid benzyl ester