(S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE

Base Information

• Chemical Name: (S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE
• CAS No.: 102922-72-5
• Molecular Formula: C26H42N2O5
• Molecular Weight: 281.309
• Mol file: 102922-72-5.mol

Synonyms:Z-L-NLE(6-OH)-OH DCHA;(S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE;N-ALPHA-BENZYLOXYCARBONYL-6-HYDROXY-L-NORLEUCINE DICYCLOHEXYLAMINE;N-alpha-Benzyloxycarbonyl-6-hydroxy-L-norleucine, (S)-N-alpha-Z-2-amino-6-hydroxyhexanoic acid Dicyclohexylamine

Chemical Property of (S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE

Chemical Property:

• Boiling Point: 510.1±50.0 °C(Predicted)
• PKA: 3.97±0.21(Predicted)
• PSA: 95.86000
• Density: 1.244±0.06 g/cm3(Predicted)
• LogP: 1.91950

Purity/Quality:

98% ^*data from raw suppliers

6-Hydroxy-N-[(phenylmethoxy)carbonyl]-L-norleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-Hydroxy-N-[(phenylmethoxy)carbonyl]-L-norleucine is an intermediate used in the synthesis of Lysine Norleucine (L488750), which is a lysine and hydroxylysine derivatives for treatment of malignant and benign tumors.

Technology Process of (S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE

There total 8 articles about (S)-N-ALPHA-Z-2-AMINO-6-HYDROXYHEXANOIC ACID DICYCLOHEXYLAMINE 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: 94.0%

N2-[(benzyloxy)carbonyl]-L-lysine (2212-75-1) → (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid (102922-72-5)

Guidance literature:

With sodium nitroprusside; sodium hydroxide; In water; at 60 ℃;

DOI:10.1021/jm400792m

Reference yield: 87.0%

d(OBzl)OH*DCHAZ- → Z-Ahc-OH (32245-65-1,102922-72-5)

Guidance literature:

With lithium borohydride; In tetrahydrofuran;

Reference yield: 84.0%

(S)-2-amino-6-hydroxyhexanoic acid (6033-32-5) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid (102922-72-5)

Guidance literature:

With sodium hydroxide; sodium carbonate; at 0 - 5 ℃; for 3h;

DOI:10.1021/jm00159a015

upstream raw materials:

N₂-[(benzyloxy)carbonyl]-L-lysine

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

benzyl chloroformate

2(S)-2-amino-6-(benzylideneamino)hexanoic acid

Downstream raw materials:

8-benzyl 1-ethyl (7S)-7-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}-2-cyanooctanedioate

8-benzyl 1-ethyl (7S)-7-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}-2-({[(tert-butoxy)carbonyl]amino}methyl)octanedioate

(2S)-2-<(Benzyloxycarbonyl)amino>-6-hydroxyhexanoic acid methyl ester

C₂₅H₃₀N₂O₄

Refernces

• 1、 Baldwin, Jack E.,Killin, Stephen J.,Adlington, Robert M.,Spiegel, Udo. "SYNTHESIS OF N-BENZYLOXYCARBONYL-L-α-AMINOADIPIC ACID, α-BENZYL ESTER". . p. 2633 - 2636. Retrieved 1988.
• 2、 -. "MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS". Paragraph 0436. . Retrieved 2019/05/02.