201348-48-3

Upstream product

• 191543-69-8 1,2-anhydro-3,5-di-O-benzyl-α-D-ribofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 685137-17-1 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)thymine 
• 561055-45-6 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 65-71-4 thymin 
• 581795-68-8 3,5-di-O-benzyl-1,2-O-thiocarbonyl-α-D-ribo-furanose 
• 5460-57-1 5-O-benzoyl-1,2-O-isopropylidene-β-D-arabinofuranose 
• 56607-40-0 methyl D-arabinofuranoside 
• 201348-41-6 methyl 5-O-benzoyl-α-D-arabinofuranoside 
• 98-88-4 benzoyl chloride 
• 131139-02-1 (3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 

Downstream Products

• 685137-31-9 1-(3',5'-di-O-benzyl-2'-O-mesyl-β-D-ribo-furanosyl)thymine 
• 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

Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides

Pyrimidine nucleosides are synthesized by using propargyl 1,2-orthoesters and Au(III) salt as a catalyst. Strategically positioned 1,2-orthoesters are found to yield only 1,2-trans nucleosides and enable preparation of 2′-OH containing pyrimidine nucleosides. The glycosyl donor employed in this study is stable and easily accessible. The identified high-yielding protocol is mild, diastereoselective, and catalytic.

Highly β-stereoselective nucleosidation from α-D-xylo- and α-D-ribo-furanose 1,2-thiocarbonates

Cyclic 1,2-thiocarbonates of α-D-xylo- and α-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording β-nucleosides with complete stereoselectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an SN2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl) acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1′ were ascertained by chemical correlation synthesizing the corresponding 2,2′-anhydro-nucleosides.

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.