(2R,5R)-2,6-diamino-5-hydroxyhexanoic acid

Base Information

• Chemical Name: (2R,5R)-2,6-diamino-5-hydroxyhexanoic acid
• CAS No.: 18899-31-5
• Molecular Formula: C₆H₁₄N₂O₃
• Molecular Weight: 162.189
• DSSTox Substance ID: DTXSID801313610
• Nikkaji Number: J38.543C
• Wikidata: Q27133215
• Metabolomics Workbench ID: 63321

Synonyms:threo-5-hydroxy-D-lysine;(5R)-5-hydroxy-D-lysine;D-aHyl;allo-hydroxy-D-lysine;allo-5-hydroxy-D-lysine;(2R,5R)-2,6-diamino-5-hydroxyhexanoic acid;(R,R)-delta-hydroxy-alpha,epsilon-diaminocaproic acid;2,6-diamino-2,3,4,6-tetradeoxy-L-threo-hexonic acid;18899-31-5;D-allo-Hydroxylysine;SCHEMBL2329815;CHEBI:64316;DTXSID801313610;EN300-6735665;Q27133215

Chemical Property of (2R,5R)-2,6-diamino-5-hydroxyhexanoic acid

Chemical Property:

• XLogP3: -4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 162.10044231
• Heavy Atom Count: 11
• Complexity: 129

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)C(CN)O
• Isomeric SMILES: C(C[C@H](C(=O)O)N)[C@H](CN)O

Technology Process of (2R,5R)-2,6-diamino-5-hydroxyhexanoic acid

There total 47 articles about (2R,5R)-2,6-diamino-5-hydroxyhexanoic 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: 90.0%

(2S,5R)-2,6-diazido-5-hydroxyhexanoic acid → (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; at 20 ℃; for 15h; under 760.051 Torr;

DOI:10.1039/c4ob01220h

Reference yield:

L-lysine (56-87-1,3506-25-0) → (2S,5S)-5-hydroxylysine (18899-29-1,28902-93-4) + (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) + (2S)-4-hydroxylysine (15574-69-3) + (2S)-2,6-diamino-3-hydroxyhexanoic acid

Guidance literature:

With oxygen; In water; γ-Irradiation;

DOI:10.1021/tx980118h

Reference yield:

type I collagen from Bester sturgeon scales → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-serin (56-45-1,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) + L-arginine (74-79-3,25212-18-4) + S,S-cystine (349-46-2) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + glycine (56-40-6,18875-39-3,25718-94-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + L-histidine (71-00-1)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1016/j.foodchem.2014.03.075

upstream raw materials:

(3R,5R,6S)-3-[2-((R)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-5-yl)-ethyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(2S,5R)-(-)-tert-butyl-6-amino-2-[(tert-butoxycarbonyl)amino]-5-hydroxyhexanoate

(R)-5-((S)-3-Amino-3-carboxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

Downstream raw materials:

(2S,5R)-5-hydroxy-2-piperidinecarboxylic acid

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid

Δ¹-pyrroline-5-carboxylate

DL-threo-N²,N⁶-bis-(2,4-dinitro-phenyl)-5-hydroxy-lysine lactone

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