17676-20-9Relevant articles and documents
Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside
Hanaya, Tadashi,Koga, Yuko,Kawamoto, Heizan,Yamamoto, Hiroshi
scheme or table, p. 581 - 591 (2009/09/08)
Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-rib
4'-Thionucleosides via in situ pyranose-furanose rearrangements: A short synthesis of the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar
Jandu,Selwood
, p. 5170 - 5173 (2007/10/02)
Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed O-S rearrangement produced methyl 2-deoxy-3-O,4-S-carbonyl-4-thio-β-D- ribopyranoside (3a) and the 3-O,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-O,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agenet 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in situ pyranoside rearrangement of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowes H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-O-carbamoyl-2-deoxy-3-thio-β-D- ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2- (hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.
A CONVENIENT METHOD FOR THE PREPARATION OF METHYL 2-DEOXY-β-D-ERYTHRO-PENTOPYRANOSIDE
Inokawa, Saburo,Mitsuyoshi, Toshiyuki,Kawamoto, Heizan,Yamamoto, Hiroshi,Yamashita, Mitsuji
, p. 321 - 323 (2007/10/02)
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