Nebramycin III

Base Information

• Chemical Name: Nebramycin III
• CAS No.: 31077-70-0
• Molecular Formula: C18H36 N4 O11
• Molecular Weight: 484.504
• UNII: 9R6480TQ34
• Metabolomics Workbench ID: 66177
• Nikkaji Number: J87.138I
• Wikidata: Q27140226
• Mol file: 31077-70-0.mol

Synonyms:Nebramycin III;Nebramycin factor 3;31077-70-0;3''-deamino-3''-hydroxykanamycin B;NK 1012-1;3"-Deamino-3"-hydroxykanamycin B;9R6480TQ34;(2S,3R,4S,5S,6R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl alpha-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-[(1S,2S,3R,4S,6R)-3-[(2R,3R,4R,5S,6R)-6-(aminomethyl)-3-azanyl-4,5-bis(oxidanyl)oxan-2-yl]oxy-4,6-bis(azanyl)-2-oxidanyl-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;NEBRAMYCIN III, (+)-;UNII-9R6480TQ34;CHEBI:72990;AMINOGLYCOSIDE NK-1012-1;'3"-deamino-3"-hydroxykanamycin B';Streptamine, O-2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-4)-O-(alpha-D-glucopyranosyl-(1-6))-2-deoxy-, D-;C21254;Q27140226;CK0;D-STREPTAMINE, O-2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(.ALPHA.-D-GLUCOPYRANOSYL-(1->6))-2-DEOXY-;O-2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(.ALPHA.-D-GLUCOPYRANOSYL-(1->6))-2-DEOXY-D-STREPTAMINE

Chemical Property of Nebramycin III

Chemical Property:

• Vapor Pressure: 4.56E-29mmHg at 25°C
• Boiling Point: 793°Cat760mmHg
• Flash Point: 433.4°C
• PSA: 282.61000
• Density: 1.62g/cm³
• LogP: -4.49020
• XLogP3: -6.9
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 484.23805798
• Heavy Atom Count: 33
• Complexity: 638

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N

Technology Process of Nebramycin III

There total 8 articles about Nebramycin III 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: 71.0%

(2R,3S,4R,5R,6R)-5-Azido-2-azidomethyl-6-[(1R,2S,3S,4R,6S)-4,6-diazido-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4-diol (671809-27-1) → 3''-deamino-3''-hydroxy-kanamycin B (31077-70-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; water; ethyl acetate; at 20 ℃; for 48h; under 2585.74 Torr;

DOI:10.1021/ol0363927

Reference yield:

3''-deamino-3''-oxo-kanamycin B → 3''-deamino-3''-hydroxy-kanamycin B (31077-70-0)

Guidance literature:

With ΔgenD2 mutant of GenD2 dehydrogenase; In aq. buffer; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.chembiol.2014.12.012

Reference yield:

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside (131531-76-5) → 3''-deamino-3''-hydroxy-kanamycin B (31077-70-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / 3 Angstroem molecular sieves; N-iodosuccinimide; TESOTf / CH₂Cl₂ / 1.5 h / -78 °C

2: 96 percent / TFA / H₂O / 0.03 h

3: 71 percent / H₂ / Pd(OH)2/C / ethyl acetate; H₂O; methanol / 48 h / 20 °C / 2585.74 Torr

With N-iodo-succinimide; 3 A molecular sieve; hydrogen; triethylsilyl trifluoromethyl sulfonate; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/ol0363927

upstream raw materials:

(2R,3S,4R,5R,6R)-5-Azido-2-azidomethyl-6-[(1R,2S,3S,4R,6S)-4,6-diazido-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4-diol

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside

1,3,2′,6′-tetraazidoneamine

kananmycin B

Refernces

• 1、 Chou, Chien-Hung,Wu, Chung-Shieh,Chen, Ching-Hui,Lu, Lung-Dai,Kulkarni, Suvarn S.,Wong, Chi-Huey,Hung, Shang-Cheng. "Regioselective Glycosylation of Neamine Core: A Facile Entry to Kanamycin B Related Analogues". . p. 585 - 588. Retrieved 2007/10/03.