beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-

Base Information

• Chemical Name: beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-
• CAS No.: 22976-86-9
• Deprecated CAS: 11043-75-7,29762-31-0
• Molecular Formula: C17H23 N5 O14
• Molecular Weight: 521.39
• UNII: A2468O1N7D
• DSSTox Substance ID: DTXSID30873865
• Nikkaji Number: J9.238J
• Wikidata: Q76005835
• Metabolomics Workbench ID: 94638
• ChEMBL ID: CHEMBL2424872
• Mol file: 22976-86-9.mol

Synonyms:polyoxin D;polyoxin D zinc salt;polyoxorim

Chemical Property of beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-

Chemical Property:

• Melting Point: 173-175 °C (decomp)
• Boiling Point: °Cat760mmHg
• PKA: 2.67±0.10(Predicted)
• Flash Point: °C
• PSA: 331.79000
• Density: 1.864g/cm³
• LogP: -3.96550
• XLogP3: -7.5
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 11
• Exact Mass: 521.12415042
• Heavy Atom Count: 36
• Complexity: 971

Purity/Quality:

97% ^*data from raw suppliers

PolyoxinD,?Streptomycescacaoivar.asoensisCURRENTLYUNAVAILABLE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)C(C(=O)O)NC(=O)C(C(C(COC(=O)N)O)O)N)O)O)C(=O)O
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[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)C(=O)O
• Uses: Polyoxin D,?Streptomyces cacaoi var. asoensis is a specific inhibitor of fungal chitin synthetase.

Technology Process of beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-

There total 11 articles about beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy- 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%

1-((2R,3R,4S,5R)-5-{(S)-[(S)-2-tert-Butoxycarbonylamino-2-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-carboxy-methyl}-3,4-dihydroxy-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (310904-44-0) → Polyoxin D (22976-86-9)

Guidance literature:

With trifluoroacetic acid; In methanol; water; at 20 ℃; for 3h;

Reference yield:

methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate (155154-68-0) → Polyoxin D (22976-86-9)

Guidance literature:

Multi-step reaction with 7 steps

1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / Heating

2: H₂ / Pd-C / ethyl acetate / 20 °C

3: NaHCO₃ / toluene; dioxane / 0.5 h / 20 °C

4: LiOH*H₂O / tetrahydrofuran; H₂O / 10 h / 0 °C

5: H₂ / Pd-C / methanol / 20 °C

6: i-Pr₂NEt / dimethylsulfoxide / 12 h / 20 °C

7: 90 percent / CF₃CO₂H / methanol; H₂O / 3 h / 20 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;

Reference yield:

Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-15-6) → Polyoxin D (22976-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-C / methanol / 1 h / 20 °C

2: N,N-dicyclohexylcarbodiimide / ethyl acetate / 1 h / 20 °C

3: i-Pr₂NEt / dimethylsulfoxide / 12 h / 20 °C

4: 90 percent / CF₃CO₂H / methanol; H₂O / 3 h / 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; water; dimethyl sulfoxide; ethyl acetate;

upstream raw materials:

1-((2R,3R,4S,5R)-5-{(S)-[(S)-2-tert-Butoxycarbonylamino-2-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-carboxy-methyl}-3,4-dihydroxy-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid

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

methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate

(S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Refernces