4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic acid

Base Information

• Chemical Name: 4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic acid
• CAS No.: 18710-32-2
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• DSSTox Substance ID: DTXSID601232571
• Nikkaji Number: J482.190D

Synonyms:SCHEMBL5145394;DTXSID601232571;AKOS006337450;18710-32-2;4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic acid;(2S,3S,4R)-4-amino-3-hydroxy-2-methylpentanoic acid

Chemical Property of 4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic acid

Chemical Property:

• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic acid

There total 2 articles about 4-Amino-2,4,5-trideoxy-2-methyl-D-arabinonic 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:

bleomycin-A2 (11116-31-7,62624-79-7) → (S)-2,3-diaminopropionic acid (515-94-6,1915-96-4,4033-39-0,6018-54-8) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + 4-amino-3-hydroxy-2-methyl-η-valeric acid (18710-32-2) + erythro-β-hydroxy-L-histidine hydrate (41215-80-9) + 2-amino-2-<6-amino-(4-carboxy-5-methyl-pyrimidin-2-yl)>propionic acid

Guidance literature:

With hydrogenchloride; In water; at 105 ℃; for 20h; Product distribution;

DOI:10.1016/0008-6215(88)85043-2

Reference yield:

deglycobleomycin-A2 (112317-44-9) → (S)-2,3-diaminopropionic acid (515-94-6,1915-96-4,4033-39-0,6018-54-8) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + 4-amino-3-hydroxy-2-methyl-η-valeric acid (18710-32-2) + erythro-β-hydroxy-L-histidine hydrate (41215-80-9) + 2-amino-2-<6-amino-(4-carboxy-5-methyl-pyrimidin-2-yl)>propionic acid

Guidance literature:

With hydrogenchloride; In water; at 105 ℃; for 20h; Product distribution;

DOI:10.1016/0008-6215(88)85043-2

Reference yield: 89.0%

(2S,3S,4R)-4-amino-3-hydroxy-2-methylpentanoic acid (18710-32-2) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (2S,3S,4R)-4-amino-3-hydroxy-2-methylvalerate (82692-04-4)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja9819458

upstream raw materials:

bleomycin-A₂

deglycobleomycin-A₂

Downstream raw materials:

benzyl (2S,3S,4R)-4-amino-3-hydroxy-2-methylvalerate

benzyl (2S,3S,4R)-4-<(N^α,N^im-bis(tert-butoxycarbonyl)-(S)-erythro-β-hydroxyhistidyl)amino>-3-hydroxy-2-methylvalerate

(2S,3S,4R)-4-{(2S,3R)-2-tert-Butoxycarbonylamino-3-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-3-hydroxy-propionylamino}-3-hydroxy-2-methyl-pentanoic acid methyl ester

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