• YAKHAK HOEJI
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• v.37 no.6
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• pp.591-597
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• 1993

Two new 6-azauracil dioxolane nucleosides which are related to Dioxolane T and expected to have anti-HIV activity were asymmetrically synthesized. The key intermediate 8 have been synthesized in ten steps from D-mannose and condensed with 6-azauracil to give 13 and 14 after desilylation, respectively.

• YAKHAK HOEJI
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• v.38 no.6
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• pp.775-781
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• 1994

$({\pm})-Dioxolane-T$ and$({\pm})-BCH-189$ are know to possess anti-HIV activities, and less to xicities compared to other dideoxynucleoside AIDS drugs. We have synthesized 34 different enantiomerically pure nucleosides by glycosylation of L-1,3-dioxolanyl acetate and L-1,3-oxathiolanyl acetate sugar moieties with uracil or 6-azauracil with alkyl chains$(C_1-C_3)$ on 5 or 6 position.

• YAKHAK HOEJI
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• v.38 no.6
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• pp.703-711
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• 1994

We synthesized D-1,3-dioxolanyl acetate from D-mannose using Frazer-Reide reaction and D-1,3-oxathiolanyl acetate from either D-mannose or D-galactose in good yields. These acetates were conjugated with various disilylated pyrimidine base using trimethylsilyl trifluoromethane sulfonate as a Lewis acid catalyst to obtain 32 different D-nucleosides.

• Bulletin of the Korean Chemical Society
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• v.32 no.2
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• pp.411-416
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• 2011

Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-group with antiviral enhancement, novel 4'-hydroxymethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were designed and synthesized from 2,2-dimethyl-1,3-dioxolane-4-ethanol (5) using reiterative Grignard addition and ring-closing metathesis (RCM) as key reactions. The synthesized adenosine phosphonic acids analogues (22) and (23) were subjected to antiviral screening against HIV-1. Compound (23) exhibited moderate anti-HIV activity ($EC_50$ = 8.61 ${\mu}M$) in the CEM cell line.

• Archives of Pharmacal Research
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• v.17 no.5
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• pp.386-388
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• 1994