Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Mechanism of antiviral action of 1,3-oxathiolane nucleosides, 3TC ( 1 ) and FTC ( 2 ), as chain terminators.

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: First synthesis of (±)-BCH-189 ( 1c ) by Belleau et al.

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Enantioselective synthesis of 3TC ( 1 ).

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Synthesis of cis- diastereomer 3TC ( 1 ) from oxathiolane propionate 44 .

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Synthesis of (±)-BCH-189 ( 1c ) via SnCl 4 -mediated N-glycosylation of 8 .

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Synthesis of (+)-BCH-189 ( 1a ) via TMSOTf-mediated N-glycosylation of 20 .

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Synthesis of 3TC ( 1 ) from oxathiolane precursor 20a .

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Synthesis of 3TC ( 1 ) via TMSI-mediated N-glycosylation.

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques:

Journal: Beilstein Journal of Organic Chemistry

Article Title: Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

doi: 10.3762/bjoc.17.182

Figure Lengend Snippet: Enzymatic resolution of the monophosphate derivative 116 for the synthesis of (−)-BCH-189 ( 1 ) and (+)-BCH-189 ( 1a ).

Article Snippet: Separation by chromatography and deprotection with TBAF in THF afforded the (−)-isomer 3TC ( 1 , EC50 = 0.07 µM in CEM cells) and the trans -isomer 1b .

Techniques: