Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside

Tetrahedron

Volumn 53, Issue 24, 1997, Pages 8085-8104

  Faul, Margaret M ^a   Huff, Bret E ^a   Dunlap, Steven E ^a   Frank, Scott A ^a   Fritz, James E ^a   Kaldor, Stephen W ^a   LeTourneau, Michael E ^a   Staszak, Michael A ^a   Ward, Jeffrey A ^a   Werner, John A ^a   Winneroski, Leonard L ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 18544392941     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00500-0     Document Type: Article

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79. Reference 34.
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81. R = 5.4 min (14), 7.6 min (15). Purities determined vs. standards of known purity.
82. R = 6.3 min (16), 7.0 min (18β), 7.1 min ), (18α), 7.9 min (17). Purities determined vs. standards of known purity.
83. 1H NMR).
84. 1H NMR).
85. 1H NMR (18α, doublet at 5.40 ppm; 18β, doublet at 5.60 ppm) or by HPLC (see Ref 36).
86. 1H NMR).
87. A reference sample of 18α was prepared in 63% yield by reduction of the phenylthionocarbonate derivative of 16 (tris(trimethylsilyl)silane, AIBN, toluene, 80 °C, 2 h).
88. The solvent volumes and the inverse quench are critical to avoid a gelatinous suspension of aluminum salts upon workup.
89. R = 10.8 min (23), 13.2 min (20), 14.8 min (22), 16.9 min (21). Purities determined vs. standards of known purity.
90. R = (7.3 min, 1), 6.7 min (C-3′ β-isomer), 5.3 min (C-1′α-isomer).
91. HPLC conditions for analysis of 33, 34, 31, 35, 36, 37, 23, and 1: Supelcosil LC-ABZ (25 cm), gradient of 40% acetonitrile/60% pH 7 phosphate buffer for 5 min to 70/30 over 5 min, hold for 5 min at 70/30 then return to 40/60 over 5 min, 1.5 mL/min, 210 nm. Purities determined vs. standards of known purity.