Negamycin

Base Information

• Chemical Name: Negamycin
• CAS No.: 33404-78-3
• Molecular Formula: C9H20 N4 O4
• Molecular Weight: 248.282
• Hs Code.: 2928000090
• UNII: B15L87Q2HQ
• DSSTox Substance ID: DTXSID701043349
• Nikkaji Number: J17.719I
• Wikidata: Q27274241
• Metabolomics Workbench ID: 118351
• ChEMBL ID: CHEMBL78628
• Mol file: 33404-78-3.mol

Synonyms:(2-((3R,5R)-3,6-diamino-5-hydroxyhexanoyl)-1-methylhydrazino) acetic acid;negamycin;negamycin, (threo-D)-isomer

Chemical Property of Negamycin

Chemical Property:

• Melting Point: 110-120° (dec)
• PKA: pKa values after treatment with HCl-methanol: 3.55, 8.10, 9.75(
• PSA: 145.40000
• Density: 1.303g/cm³
• LogP: -0.29800
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 248.14845513
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

99%, ^*data from raw suppliers

NEGAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Negamycin

There total 98 articles about Negamycin 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: 98.0%

(R)-tert-butyl (R)-5-[2-(tert-butoxycarbonylamino)-3-{(tert-butoxycarbonylmethyl)methylaminocarbamoyl}propyl]-2,2-dimethyloxazolidine-3-carboxylate (1037825-22-1) → negamycin (33404-78-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 0 ℃; for 2h;

DOI:10.1039/b801498a

Reference yield: 96.0%

[N'-((3R,5R)-3-Amino-6-benzyloxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester → negamycin (33404-78-3)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; for 12h; under 2250.2 Torr; Ambient temperature;

DOI:10.1055/s-1992-26142

Reference yield: 94.0%

2-((3R,5R)-2-benzyloxycarbonyl-5-(chloromethyl)isoxazolidinyl)acetic acid (1613376-41-2) → negamycin (33404-78-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; water; at 20 ℃; for 24h; under 2068.65 Torr;

DOI:10.1039/c4ob00537f

upstream raw materials:

{N'-[(3R,5R)-3,6-Diazido-5-(tert-butyl-dimethyl-silanyloxy)-hexanoyl]-N-methyl-hydrazino}-acetic acid benzyl ester

benzyl 2-(1-methylhydrazinyl)acetate

(3R,5R)-6-Azido-3-benzyloxycarbonylamino-5-(tetrahydro-pyran-2-yloxy)-hexanoic acid

benzyl (3R,5R)-<2-<methyl>isoxazolidin-3-yl>acetyl>-1-methylhydrazino>acetate

Downstream raw materials:

[N'-((3R,5S)-3,6-Bis-benzyloxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazino]-acetic acid methyl ester

[N'-((3R,5S)-3,6-Bis-benzyloxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazino]-acetic acid

Refernces

• 1、 -. "Full-synthesizing method of natural product (+)-negamycin". . . Retrieved 2017/09/18.
• 2、 Davies, Stephen G.,Ichihara, Osamu,Roberts, Paul M.,Thomson, James E.. "Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition". experimental part. p. 216 - 227. Retrieved 2011/03/17.