Piomycin B

Base Information

• Chemical Name: Piomycin B
• CAS No.: 22976-90-5
• Molecular Formula: C₁₆H₂₃N₅O₁₂
• Molecular Weight: 477.385
• DSSTox Substance ID: DTXSID801101384
• Nikkaji Number: J16.347C
• Wikidata: Q76421997
• Mol file: 22976-90-5.mol

Synonyms:polyoxin L

Chemical Property of Piomycin B

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 289.75000
• Density: 1.771g/cm³
• LogP: -4.33890
• XLogP3: -7.7
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 10
• Exact Mass: 477.13432119
• Heavy Atom Count: 33
• Complexity: 837

Purity/Quality:

99% ^*data from raw suppliers

POLYOXIN L 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)C(C(=O)O)NC(=O)C(C(C(COC(=O)N)O)O)N)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)[C@@H](C(=O)O)NC(=O)[C@H]([C@@H]([C@H](COC(=O)N)O)O)N)O)O

Technology Process of Piomycin B

There total 22 articles about Piomycin B 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%

(S)-[(S)-2-tert-Butoxycarbonylamino-2-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid (205449-16-7) → Polyoxin L (22976-90-5)

Guidance literature:

With trifluoroacetic acid; In methanol;

DOI:10.3987/COM-97-S(N)59

Reference yield: 56.0%

C37H54N6O15S → Polyoxin L (22976-90-5)

Guidance literature:

C₃₇H₅₄N₆O₁₅S; With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; In 1,2-dimethoxyethane; water; at 0 ℃; for 0.5h;

With trifluoroacetic acid; In 1,2-dimethoxyethane; water; at 20 ℃; for 2h;

DOI:10.1002/anie.201706671

Reference yield:

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester (205449-09-8) → Polyoxin L (22976-90-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 45 percent / K₂CO₃ / methanol / 0.67 h / 0 °C

2: 90 percent / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

3: dimethylformamide / 1 h

4: 87 percent / K₂CO₃ / methanol / 1 h / 0 °C

5: pyridine / CH₂Cl₂ / 0.33 h / 0 °C

6: NaN₃ / dimethylformamide / 0.5 h / 20 °C

7: H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 20 °C

8: Et₃N / dioxane / 1.25 h / 20 °C

9: 94 percent / HF; H₂O; pyridine / 3 h / 20 °C

10: Et₃N; pyridine / tetrahydrofuran; diethyl ether / 1 h / -20 °C

11: NH₃ / methanol / 0.5 h / 0 °C

12: 82 percent / Ti(O-i-Pr)4 / benzene / 12 h / Heating

13: 99 percent / H₂ / 10 percent Pd/C / methanol / 0.5 h / 20 °C

14: DCC / ethyl acetate / 1 h / 0 °C

15: i-Pr₂NEt / dimethylsulfoxide / 24 h / 20 °C

16: 94 percent / CF₃SO₃H; H₂O / methanol / 24 h / 20 °C

With pyridine; titanium(IV) isopropylate; sodium azide; trifluorormethanesulfonic acid; hydrogen fluoride; ammonia; water; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Deacetylation / 2: Esterification / 3: Substitution / 4: Deacetylation / 5: Esterification / 6: Substitution / 7: Catalytic hydrogenation / 8: Acylation / 9: desilylation / 10: Carbonylation / 11: Substitution / 12: Substitution / 13: Hydrogenolysis / 14: Substitution / 15: Acylation / 16: Hydrolysis;

DOI:10.1055/s-1999-3563

upstream raw materials:

(S)-[(S)-2-tert-Butoxycarbonylamino-2-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid

methyl 5-O-(aminocarbonyl)-2-<(N-tert-butoxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-xylonate

5-O-(aminocarbonyl)-2-[((1,1-dimethylethyl)oxycarbonyl)amino]-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

methyl 2-N-[(tert-butoxycarbonyl)amino]-2-deoxy-3,4-O-isopropylidene-L-xylonate

Refernces

• 1、 Uchida, Kimio,Kato, Keisuke,Akita, Hiroyuki. "A convenient synthesis of a N-protected l-carbamoylpolyoxamic acid derivative: Total synthesis of (+)-polyoxin J and (+)-polyoxin L1". . p. 1678 - 1686. Retrieved 2007/10/03.