201348-64-3

Upstream product

• 112-76-5 Stearoyl chloride 
• 201348-63-2 (2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-2-methyl-6-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-ol 
• 100-39-0 benzyl bromide 

Downstream Products

• 528586-05-2 3',5'-di-O-benzyl-2'-O-(2,3-di-O-benzyl-4-O-stearoyl-α-L-fucopyranosyl)uridine 
• 201348-65-4 3',5'-di-O-benzyl-2'-O-(2,3-di-O-benzyl-4-O-stearoyl-α-L-fucopyranosyl)thymidine 

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.