4237-19-8

Upstream product

• 98-88-4 benzoyl chloride 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 

Downstream Products

• 56570-83-3 Benzoic acid (2R,3R,4R)-4-hydroxy-5-methoxy-2-methyl-tetrahydro-furan-3-yl ester 
• 4152-80-1 5-deoxy-3-O-benzoyl-1,2-di(O-acetyl)-β-D-xylofuranose 
• 4152-81-2 5-deoxy-3-O-benzoyl-1,2-di(O-acetyl)-α-D-xylofuranose 
• 1028945-18-7 C₁₉H₂₄O₈ 

Relevant academic research and scientific papers

First total synthesis of a naturally occurring iodinated 5′-deoxyxylofuranosyl marine nucleoside

4-Amino-7-(5′-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d] pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrueggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1, 2-O-diacetyl-3-O-benzoyl-D- xylofuranose. Its absolute configuration was confirmed.

Kinetics of methylation of methyl 5-deoxy-α/β-D-xylofuranosides

The kinetics of methylation of methyl 5-deoxy-α-D-xylofuranoside (1), methyl 5-deoxy-β-D-xylofuranoside (2) and their partly methylated derivatives with methyl iodide in the presence of sodium hydroxide in acetonitrile was studied. The reaction rate was i