80229-19-2

Upstream product

• 67-56-1 methanol 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 100-39-0 benzyl bromide 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 85951-12-8 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 
• 58-86-6 D-xylose 
• 167500-61-0 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose 
• 634914-79-7 methyl 3,5-O-benzylidene-α-D-xylofuranoside 

Downstream Products

• 174833-53-5 methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-α-D-arabino-pentofuranoside 
• 174833-51-3 methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside 
• 160882-24-6 methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside 

Relevant academic research and scientific papers

Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring α-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-d- arabinitol (3), with cyclic sulfates (8, 9, and 10), and their α-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the α-glucosidase inhibitory activity. A practical synthetic route to 3 starting from d-xylose is also described.

A Novel Synthesis of 2′-Modified 2′-Deoxy-4′-thiocytidines from D-Glucose

Novel 2′-deoxycytidine antimetabolites, specifically several 2′-modified 2′-deoxy-4′-thiocytidines, were synthesized as potential new antineoplastic agents. Methyl 3-O-benzylxylofuranoside was converted to a 1,4-anhydro-4-thioarabitol 24. Protection of the primary alcohol of 24 gave a common intermediate (15) which was useful for the synthesis of various 2′-modified 2′-deoxy-4′-thionucleosides. Oxidation of the secondary hydroxyi group of 15, followed by the Wittig reaction or treatment with (diethylamido)sulfur trifluoride (DAST) produced 2-deoxy-2-methylene (26) and 2-deoxy-2,2-difluoro (34) derivatives, respectively. Unique Pummerer-type glycosylation between the corresponding sulfoxides and trimethylsilylated N4-acetylcytosine produced 2′-deoxy-2′-methylene- (10) and 2′-deoxy-2′,2′-difluoro-4′-thiocytidines (11). On the other hand, treatment of 15 with DAST introduced a fluorine atom with retention of the 2′-stereochemistry, yielding 40. In contrast, the Mitsunobu reaction of 3-O-benzoyl derivative 53 which was obtained from 15 in five steps, using diphenylphosphoryl azide gave azide derivative 54 with inverted stereochemistry. These derivatives were converted to the corresponding 1-O-acetyl derivatives via the usual Pummerer rearrangement, which were in turn used to synthesize 4′-thiocytidines 12 and 58. Among the 2′-modified 4′-thiocytidines obtained, 2′-methylene (10) and 2′-fluoro (12) derivatives were found to have potent antineoplastic properties in vitro.

HYDROGENOLYSIS OF 3,5-O-BENZYLIDENE ACETALS WITH THE LiAlH4-AlCl3 REAGENT IN METHYL D-XYLOFURANOSIDES

The hydrogenolysis of methyl 3,5-O-benzylidene-α- and -β-D-xylofuranoside derivatives with the LiAlH4-AlCl3 reagent gave 5-benzyl ethers as main products.In some cases the attack of the reagent occured at the ring oxygen of the furanoside skeleton to yiel