402564-07-2

Upstream product

• 377773-02-9 1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-methanesulfonylmethyl-5-O-(4-methoxytrityl)-β-D-ribo-pentofuranosyl]uracil 
• 377773-01-8 1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-hydroxymethyl-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil 
• 377773-00-7 1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-methylene-5-O-(4-monomethoxytrityl)-β-D-erythro-pentofuranosyl]uracil 
• 402564-06-1 1-[3-C-azidomethyl-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytrityl)-β-D-ribo-pentofuranosyl]uracil 

Downstream Products

• 661485-46-7 acetic acid 1-[3-(benzyloxycarbonylamino-methyl)-4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-nitro-ethyl ester 
• 661485-45-6 [4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(1-hydroxy-2-nitro-ethyl)-tetrahydro-furan-3-ylmethyl]-carbamic acid benzyl ester 
• 661485-48-9 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine 
• 661485-47-8 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5',3'-dideoxy-5'-nitromethyluridine 
• 661485-44-5 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-3'-deoxyuridine 
• 906795-53-7 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-3'-deoxy-5'-O-(4-methoxytrityl)uridine 

Relevant academic research and scientific papers

Stereoselectivity in the synthesis of 3′-deoxy-3′-C-(hydroxymethyl)uridines by hydroboration and conversion into a building block for various 3′-deoxy-3′-C-(methylene)uridine analogues

The stereoselectivity in hydroboration of 3′-deoxy-3′-C-(methylene)uridine derivatives has been studied. Hydroboration of 3′-deoxy-3′-C-(methylene)uridine derivatives gave two 3′-deoxy-3′-C-hydroxymethyl stereoisomers (with ribo or xylo configuration). The influence of reagent (BH3·Me2S, or 9-borabicyclo[3.3.1]nonane (9-BBN-H)) and solvent (THF, toluene, or hexane) was investigated. Use of BH3·Me2S gave the xylo isomer as the main product. The highest preference for the ribo isomer was obtained by use of 9-BBN-H in hexane. Furthermore, 4-methoxytrityl protection of the hydroxy function at the 5′-position resulted in better stereoselectivity than that obtained by tert-butyldimethylsilyl protection, when 9-BBN-H was used as reagent. At best, hydroboration of 1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-methylene-5-O-(4-methoxytrityl)- β-D-erythro-pentofuranosyl]uracil (3b) using 9-BBN-H in hexane gave a ribo to xylo (4b to 5b) isomer ratio of 82:18. The ribo isomer was converted into the corresponding mesylate 6 to allow for further functionalization. Subsequent substitution with azide and reduction afforded 1-[3-C-aminomethyl-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytrityl)- β-D-ribo-pentofuranosyl]uracil (8) in good overall yield (43% over 6 steps). Wiley-VCH Verlag GmbH, 2001.