5627-05-4

Basic information

• Product Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
• Synonyms: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one;dihydrouridine
• CAS NO: 5627-05-4
• Molecular Formula: C₉H₁₄N₂O₆
• Molecular Weight: 246.22
• Mol File: 5627-05-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.614g/cm³
• Refractive Index: 1.613
• PKA: 12.40±0.20(Predicted)
• CAS DataBase Reference: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one(5627-05-4)
• EPA Substance Registry System: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one(5627-05-4)

Safety Data

• Hazardous Substances Data: 5627-05-4(Hazardous Substances Data)

Usage

Uses

5,6-Dihydrouridine is an intermediate used in the synthesis of 3,4,5,6-Tetrahydrouridine (>80%) (T310250), which is a derivative of Uridine (U829910). Tetrahydrouridine (THU) is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.

Definition

ChEBI: The uridine derivative obtained by formal hydrogenation of the endocyclic double bond in the uracil ring.

InChI:InChI=1/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m0/s1

Upstream product

• 87418-77-7 5'-O-(tert-butyldimethylsilyl)uridine 
• 820212-22-4 5'-O-tert-butyldimethylsilyl-2',3'-O-bis(benzyloxycarbonyl)uridine 
• 820212-19-9 2′,3′-O-bis-(benzyloxycarbonyl)uridine 
• 3257-71-4 2',3'-O-(benzylidene)uridine 
• 58-96-8 uridine 

Downstream Products

• 59279-52-6 2',3'-O-isopropylidene-5,6-dihydrouridine 
• 19149-48-5 1-(β-D-ribofuranosyl)hexahydropyrimidin-2-one 
• 18771-50-1 Tetrahydrouridine 
• 79974-74-6 2',3'-Bis-O-(tert-butyldiphenylsilyl)-5,6-dihydro-5'-O-(4-methoxytrityl)uridin 
• 79974-75-7 2',3'-Bis-O-(tert-butyldiphenylsilyl)-5,6-dihydrouridin 
• 79974-73-5 2',3'-Bis-O-(tert-butyldimethylsilyl)-5,6-dihydro-5'-O-(4-methoxytrityl)uridin 
• 79974-72-4 3'-O-(tert-Butyldimethylsilyl)-5,6-dihydro-5'-O-(4-methoxytrityl)uridin 
• 79536-96-2 2'-O-t-Butyldimethylsilyl-5'-O-monomethoxytrityl-N⁶-benzoyl-5,6-dihydro-uridin 
• 97327-35-0 1-(3,5-dimesyloxy-β-D-arabinofuranosyl)-2-thio-5,6-dihydrouracil 
• 97327-34-9 2,2'-anhydro-1-(3,5-dimesyloxy-β-D-arabinofuranosyl)-5,6-dihydrouracil 
• 162825-91-4 C₅₄H₆₀ClN₄O₁₇P 
• 162825-86-7 1-[(2R,3R,4R,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-dihydro-pyrimidine-2,4-dione 
• 173169-16-9 5,6-dihydro-2'-O-<2-(4-nitrophenyl)ethylsulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 162825-83-4 5,6-dihydro-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 

Relevant articles and documents

Infared spectra and tautomeric structure of nucleosides and nucleotides in D2O solution. II.

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Rhodium-catalyzed reductive modification of pyrimidine nucleosides, nucleotide phosphates, and sugar nucleotides

Nucleosides and nucleotides are a group of small molecule effectors and substrates which include sugar nucleotides, purine and pyrimidine-based nucleotide phosphates, and diverse nucleotide antibiotics. We previously reported that hydrogenation of the nucleotide antibiotic tunicamycin leads to products with reduced toxicity on eukaryotic cells. We now report the hydrogenation of diverse sugar nucleosides, nucleotide phosphates, and pyrimidine nucleotides. UDP-sugars and other uridyl and thymidinyl nucleosides are quantitatively reduced to the corresponding 5,6-dihydro-nucleosides. Cytidyl pyrimidines are reduced, but the major products are the corresponding 5,6-dihydrouridyl nucleosides resulting from a deamination of the cytosine ring.

TUNICAMYCIN RELATED COMPOUNDS WITH ANTI-BACTERIAL ACTIVITY

Tunicamycin related compounds having an acyl chain double bond reduced and/or having an acyl chain double bond and an uracil ring double bond reduced are described as well as methods of making these tunicamycin related compounds. These tunicamycin related compounds are not toxic to eukaryotic cells and can be used to kill Gram-positive bacteria, alone or in combination with other antibiotics. Use of these tunicamycin related compounds to kill Gram-positive bacteria, treat Gram-positive bacterial diseases, and disinfect objects or surfaces are described. In addition, naturally-occurring streptovirudin compounds are not toxic to eukaryotic cells and can be used to kill Gram-positive bacteria, alone or in combination with other antibiotics.

Facile deprotection of O-Cbz-protected nucleosides by hydrogenolysis: An alternative to O-benzyl ether-protected nucleosides

(Chemical Equation Presented) Because of side-reactions encountered during hydrogenolysis, benzyl ethers are usually not an effective protecting group for nucleosides. Benzyloxycarbamates provide an alternative to traditional benzyl ethers for protection of nucleoside hydroxyl groups, as they are much more labile to hydrogenolysis. Deprotection conditions using transfer hydrogenolysis are described that avoid the reduction of the pyrimidine nucleobase during deblocking of O-Cbz-protected nucleosides. Additionally, an experiment is described that suggests the nucleobase component of a nucleoside is responsible for the sluggish hydrogenolysis of nucleosides.