24695-48-5

Basic information

• Product Name: uracil polyoxin C
• Synonyms: uracil polyoxin C;1-(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-1-yl)-5-amino-1,5-dideoxy-β-D-allofuranuronic acid;5-Amino-1-(1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-yl)-1,5-dideoxy-β-D-allofuranuronic acid;5-Amino-1-(3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-1,5-dideoxy-β-D-allofuranuronic acid;Nikkomycin C;Nikkomycin Cz
• CAS NO: 24695-48-5
• Molecular Formula: C₁₀H₁₃N₃O₇
• Molecular Weight: 287.22612
• Mol File: 24695-48-5.mol

Chemical Properties

• Melting Point: 241-245 °C
• Appearance: /
• Density: 1.782g/cm³
• Refractive Index: 1.679
• PKA: 2.00±0.10(Predicted)
• CAS DataBase Reference: uracil polyoxin C(CAS DataBase Reference)
• NIST Chemistry Reference: uracil polyoxin C(24695-48-5)
• EPA Substance Registry System: uracil polyoxin C(24695-48-5)

Safety Data

• Hazardous Substances Data: 24695-48-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13N3O7/c11-4(9(17)18)7-5(15)6(16)8(20-7)13-2-1-3(14)12-10(13)19/h1-2,4-8,15-16H,11H2,(H,17,18)(H,12,14,19)/t4-,5-,6+,7?,8+/m0/s1

Upstream product

• 34311-36-9 (S)-Azido-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 
• 211111-00-1 (S)-Azido-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid ethyl ester 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 127646-31-5 Phenyl (Methyl 2,3-O-isopropylidene-δ-D-allofuranosid)thiouronate 
• 155154-68-0 methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate 
• 611184-75-9 Methyl 2,3-O-Isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 
• 127646-32-6 (S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester 
• 127646-33-7 Methyl -β-D-allofuranosid>uronate 
• 127646-30-4 Methyl 5,6-Dideoxy-2,3-O-isopropylidene-6-nitro-6-(phenylthio)-β-D-ribo-hex-5(Z)-enofuranoside 
• 58934-69-3 (S)-Azido-((2R,3S,4R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester 
• 32445-75-3 D-Ribose 
• 174498-69-2 1-{(3aR,4R,6R,6aR)-6-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-1H-pyrimidine-2,4-dione 
• 174498-68-1 1-(5'-azido-5'-deoxy-2',3'-O-isopropylidene-β-D-allofuranosyl)uracil 
• 175354-46-8 2-Benzyloxycarbonylamino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-methoxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-malonic acid dibenzyl ester 

Downstream Products

• 100566-83-4 N-ε-octanoyllysyl-uracil polyoxin C 
• 131068-88-7 1-<5'-phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoyl>amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil benzyl ester 
• 74342-20-4 nikkomycine B 
• 100995-69-5 1-<5'-<(phenylalanyl-Δ^Z-dehydrophenylalanyl)amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 100995-68-4 1-<5'-<<2-(aminooxy)-3-phenylpropionyl>amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 93806-72-5 1-<5'-(L-alanylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 93806-88-3 (S)-[((S)-2-Benzyloxycarbonylamino-propionyl)-methyl-amino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 
• 93806-75-8 1-<5'-(L-alanylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 93806-87-2 1-<5'-(L-alanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 93842-00-3 1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 
• 86632-65-7 1-<5'-(L-citrullylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 

Relevant articles and documents

(1-Ethoxyvinyl)lithium in the total synthesis of thymine polyoxin C and uracil polyoxin C

A short path synthesis of the ethyl (methyl 2,3-O-isopropylidene-β-D- allofuranosid)uronate (5) and ethyl (methyl 2,3-O-isopropylidene-α-L- talofuranosid)uronate (6) from methyl 2,3-O-isopropylidene-β-D- ribopentodialdo-1,4-furanoside (3) using (1-ethoxyvinyl)lithium and its application to the total synthesis of the pyrimidine nucleosides, thymine polyoxin C (1) and uracil polyoxin C (2), are described.

Total synthesis of uradl polyoxin c

An improved synthesis of methyl (methyl 5-azido-5deoxy-2,3-O-isopropylidene-β-D-allofuranosid)uronate (7) from methyl 2,3-0-isopropylidene-β-D-rifro-pentodialdo-l,4-furanoside (6), using vinylmagnesium bromide in the key step, and its application to the total synthesis of uracil polyoxin C (1) are described.

A short path synthesis of α-hydroxy ester from aldehyde using (1-ethoxyvinyl)lithium and its application to the syntheses of thymine polyoxin c and uracil polyoxin C

A short path synthesis of the α-hydroxy esters (4 and 5) from the aldehyde (3) using (1-cthoxyvinyl)lithium and its application to the total syntheses of the pyrimidine nucleoside, thymine polyoxin C (1) and uracil polyoxin C (2), are described.

Synthesis of uracil polyoxin C from uridine

An improved procedure is reported for the asymmetric synthesis of uracil polyoxin C (UPOC) from 2',3'-O-isopropylideneuridine-5'-aldehyde. The methodology described here is based on the highly diastereocontrolled formation of 1-(β-D-allofuranosyl)uracil a

(Phenylthio)nitromethane in the Total Synthesis of Polyoxin C

The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described.Condensation of (phenylthio)nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 5 gave the (Z)-nitro olefin 6.Addition of potassium trimethylsilanoate and ozonolysis gave the α-hydroxy thioester 7, which was formed with excellent diastereoselectivity.The alcohol 7 was converted into polyoxin C (1) and uracil polyoxin C (2) via the azide 11 and base incorporation using the Vorbrueggen method.