3180-74-3

Basic information

• Product Name: 5-methyl-1-(2,3,4,6-tetra-O-acetylhexopyranosyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 3180-74-3
• Molecular Formula: C₁₉H₂₄N₂O₁₁
• Molecular Weight: 456.4007
• Mol File: 3180-74-3.mol
• Article Data: 13

Chemical Properties

• Density: 1.4g/cm³
• Refractive Index: 1.542
• CAS DataBase Reference: 5-methyl-1-(2,3,4,6-tetra-O-acetylhexopyranosyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-1-(2,3,4,6-tetra-O-acetylhexopyranosyl)pyrimidine-2,4(1H,3H)-dione(3180-74-3)
• EPA Substance Registry System: 5-methyl-1-(2,3,4,6-tetra-O-acetylhexopyranosyl)pyrimidine-2,4(1H,3H)-dione(3180-74-3)

Safety Data

• Hazardous Substances Data: 3180-74-3(Hazardous Substances Data)

Upstream product

• 65-71-4 thymin 
• 604-69-3 β-D-glucose pentaacetate 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 942428-83-3 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 1346937-18-5 C₂₇H₃₂O₁₁ 
• 83-87-4 D-glucose pentaacetate 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 3180-78-7 1-(β-D-glucopyranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 183895-65-0 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine 
• 183895-77-4 1-(2,3-di-O-acetyl-6-O-monomethoxytrityl-β-D-glucopyranosyl)thymine 
• 183436-76-2 1-(2,3-di-O-acetyl-6-O-dimethoxytrityl-β-D-glucopyranosyl)thymine 

Relevant articles and documents

The action of diethylaminosulfur trifluoride (DAST) on 1-(4,6-O-isopropylidene-β-D-glucopyranosyl)pyrimidines, a one-pot synthesis of 2,2'-anhydro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-altropyranosyl)pyrimidines

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Synthesis of pyranonucleoside-6′-triphosphates through the cyclosal-method

The high yielding synthesis of pyranonucleoside-6′-triphosphates by using the cycloSal-method is described. Synthesis of the activated cycloSal-pyranonucleoside-6′-phosphate triesters was achieved by applying a synthetic route that had been developed for the synthesis of cycloSal-(glycopyranosyl-6)-phosphates by us. The route involved regioselective 6′-tert-butyldimethylsilyl protection and exchange of the silyl protecting group by the fluorenylmethyloxycarbonyl (Fmoc) group. The 6′-Fmoc- protected derivatives were selectively converted into the cycloSal-triester. These were then very efficiently converted into triphosphates by a "titration-like" reaction with pyrophosphate. Simple purification by first ion exchange followed by reversed phase (RP) column chromatography afforded the triphosphates in very good yields. Copyright

SELECTIVE VALORIZATION OF BIOMASS SUGARS

Disclosed are methods of forming an epimer or a dehydrated isomer of a pyranose monosaccharide or a pyranose saccharide residue in an oligosaccharide or a glycoside.

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.