70613-79-5

Upstream product

• 89824-86-2 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 

Downstream Products

• 90213-74-4 2-Amino-4-chloro-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]-pyrimidine 
• 90213-73-3 2-Amino-4-chlor-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 86781-82-0 2-amino-4-methoxy-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 86781-81-9 2-amino-4-methoxy-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 90213-69-7 2,4-Dichlor-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 90213-68-6 2,4-Dichlor-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 70550-64-0 4-Chlor-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 70550-63-9 4-Chlor-2-methylthio-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 862163-51-7 2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-α-D-arabinofuranoside 
• 74895-44-6 4-Amino-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 74895-45-7 4-Amino-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 74895-43-5 4-Benzylamino-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 74895-42-4 4-Benzylamino-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 1159261-62-7 hexyl 2,3,5-tri-O-benzyl-1-thio-β-D-arabinofuranoside 

Relevant academic research and scientific papers

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Acceptor-dependent stereoselective glycosylation: 2′-CB glycoside-mediated direct β-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall

(Chemical Equation Presented) A reliable and generally applicable direct method for the stereoselective β-arabinofuranosylation employing a 2′-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosy

SYNTHESIS OF PHOSPHATE AND PHOSPHATES ISOSTERES OF FURANOSE SUGARS AS POTENTIAL ENZYME INHIBITORS

Various D-furanose monosaccharides were synthesized as possible inhibitors of the gluconeogenic enzyme fructose 1,6-bisphosphatase.These included sulfamate, phosphoramidate, and epoxy analogues of the natural substrate, fructose 1,6-diphosphate (1), and arabinose and ribose analogues of a natural inhibitor, fructose 2,6-diphosphate (2).NMR studies were conducted to establish the stereochemistry of phosphate displacement at Cl in the synthesis of arabinose 1-phosphate derivatives. β-Ribose 1,5-diphosphate (35b) was prepared with >95 percent stereoselectivity.

7-(β-D-Arabinofuranosyl)-2,4-dichloro-7H-pyrrolopyrimidine - Synthesis, Selective Displacement of Halogen, and Influence of Glyconic Protecting Groups on the Reactivity of the Aglycone

Selective N-7 glycosylation of 2,4-dichloro-7H-pyrrolopyrimidine (1a) with the arabinohalogenose 5 has been achieved yielding the β-anomer 7a in 67percent yield.Debenzylation with boron trichloride results in the formation of the 2,4-dichloronucleo

2-AMINO-7-Β-D-ARABINOFURANOSYL-4-MEYHOXY-7H-PYRROLOPYRIMIDINE: A FACILE PREPARATION AND ANOMERISATION OF A 7-DEAZAPURINE NUCLEOSIDE

Phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolopyrimidine with 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide in benzene-50percent aqueous sodium hydroxide-tetrabutylammonium hydrogensulfate gave two anomeric glycosylation products (1 and 3).Removal of the benzyl groups from 1 and 3, respectively, with boron trichloride yielded 2-ami-no-7-(α- and β-D-arabinofuranosyl)-4-methoxy-7H-pyrrolopyrimidine(4 and 2).Treatment of 2 and 4 with 2M hydrochloric acid under nitrogen caused anomerisation and demethylation without glycosylic cleavage, and reflected the extraordinary stability of pyrrolopyrimidine nucleosides towards hydrolisis.The conversion of 2 and 4 into ara-7-deazaguanosine or its α anomer was accomplished with anhydrous acid.

Synthese von Ara-Tubercidin und seiner 5'-Phosphate ueber Phasentransfer-Glycosylierung von 4-Amino-2-methylthio-7H-pyrrolopyrimidin

Phase transfer glycosylation of 4-amino-2-methylthio-7H-pyrrolopyrimidine (3a) with 2,3,5-tri-O-benzyl-1-bromo-D-arabinofuranose gives the anomeric nucleoside derivatives 4a/5a in 83percent yield.They are separated chromatographically and the ratio