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Volumn 54, Issue 20, 1989, Pages 4780-4785

Preparation of 1-(2,3-dideoxy-β-D-glycero -pent-2-enofuranosyl)thymine ((d4T)1 and 2′,3′-Dideoxyadenosine (ddA): General Methods for The Synthesis of 2′,3′-Olefinic and 2′,3′-dideoxy Nucleoside Analogues Active Against HIV

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYADENOSINE; 2',3' DIDEOXYNUCLEOSIDE;

EID: 0024418643     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00281a017     Document Type: Article
Times cited : (106)

References (35)
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    • During the preparation of this manuscript, a report appeared also outlining a Corey-Winter approach to d4U. The author showed that olefination with trimethyl phosphite occurs without methylation if oxygen is excluded from the reaction mixture and a base workup is avoided.
    • During the preparation of this manuscript, a report appeared also outlining a Corey-Winter approach to d4U. Dudycz, L. Nucleosides Nucleotides 1989, 8, 35. The author showed that olefination with trimethyl phosphite occurs without methylation if oxygen is excluded from the reaction mixture and a base workup is avoided.
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    • These methods are reported to work well on the carbohydrate precursors before nucleoside formation; see: (b) Okabe, M.; Ruen-Chu, S.; Tam, S. Y. K.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1988, 53, 4780.
    • These methods are reported to work well on the carbohydrate precursors before nucleoside formation; see: (a) Camps, P.; Cardellah, J.; Font, J.; Ortuno, R. M.; Ponsati, O. Tetrahedron 1982, 38, 2395. (b) Okabe, M.; Ruen-Chu, S.; Tam, S. Y. K.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1988, 53, 4780.
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    • During the preparation of this manuscript, a similar dioxolane-based route to 12 was reported. The authors report observations similar to our own. See
    • During the preparation of this manuscript, a similar dioxolane-based route to 12 was reported. The authors report observations similar to our own. See: Shiragami, H.; Irie, Y.; Shirae, H.; Yokozeki, K.; Yasuda, N. J. Org. Chem. 1988, 53, 5179.
    • (1988) J. Org. Chem. , vol.53 , pp. 5179
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    • Normally mL of resin is added.
    • A pH meter should be used. Normally 50–75 mL of resin is added.
    • A pH meter should be used , pp. 50-75


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