5460-57-1

Upstream product

• 108540-32-5 O⁵-Benzoyl-D-arabinose 
• 67-64-1 acetone 
• 7151-04-4 5-O-benzoyl-D-arabinose diethyl dithioacetal 
• 98-88-4 benzoyl chloride 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 56607-40-0 methyl D-arabinofuranoside 
• 201348-41-6 methyl 5-O-benzoyl-α-D-arabinofuranoside 

Downstream Products

• 19139-80-1 ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 131139-02-1 (3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 110316-24-0 3-O-benzyl-1,2-O-isopropylidene-β-D-arabino-pentodialdo-1,4-furanose 
• 174277-96-4 3-O-allyl-6-deoxy-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-altrofuranose 
• 201348-65-4 3',5'-di-O-benzyl-2'-O-(2,3-di-O-benzyl-4-O-stearoyl-α-L-fucopyranosyl)thymidine 
• 201348-48-3 1-(3',5'-di-O-benzyl-β-D-ribo-furanosyl)thymine 
• 191543-69-8 1,2-anhydro-3,5-di-O-benzyl-α-D-ribofuranose 

Relevant academic research and scientific papers

A new and efficient strategy for the synthesis of shimofuridin analogs: 2′-O-(4-O-stearoyl-α-L-fucopyranosyl)thymidine and -uridine

Two shimofuridin analogs: 2′-O-(4-O-stearoyl-α-L-fucopyranosyl)thymidine (2) and -uridine (3) have been synthesized using D-arabinose, L-fucose, thymine, uracil, and stearoyl chloride as the starting materials. The synthetic procedures involve the facile preparation of 1-(3,5-di-O-benzyl-β-D-ribofuranosyl)thymine (9) and -uracil (10) by coupling of 1,2-anhydro-3,5-di-O-benzyl-α-D-ribofuranose (8) with silylated thymine and uracil, and then stereoselective formation of the 1,2-cis (α) interglycoside bonds through condensation of the nucleoside derivatives 9 and 10 with 2-(2,3-di-O-benzyl-4-O-stearoyl-β-L-fucopyranosylsulfonyl) pyrimidine (18). The 1,2-anhydro-3,5-di-O-benzyl-α-D-ribofuranose (8) was prepared by an improved procedure from D-arabinose.

Synthesis of 2'-O-[(4''-O-stearoyl)-α-L-fucopyranosyl]thymidine: A shimofuridin analogue

A synthesis of the title compound has been achieved. The procedure involves a facile preparation of 1'-(3',5'-di-O-benzyl-β-D-ribofuranosyl)-thymine (8) with 1,2-anhydroribofuranose (7) as the glycosyl donor, stereoselective formation of a 1,2-cis (α) interglycoside bond with 4-O-stearoylated pyrimidin-2-yl 1 thio-β-L-fucopyranoside (16) as the glycosyl donor.

A facile synthesis of 5-thio-L-fucose and 5-thio-D-arabinose from D-arabinose

5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-β-D-arabino

On the Mechanism of the Chorismate Mutase Reaction

To probe the mechanistic pathway of the reaction catalyzed by chorismate mutase, the secondary tritium isotope effect at C-4 of chorismate, kH/kT, has been determined.The small inverse effect of 0.96 rules out pathways that involve g