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29.14.16.1.2 Method 2: Formation of the S/Se/Te—P Bond

DOI: 10.1055/sos-SD-029-00823

Turnbull, W. B.; Fascione, M. A.; Stalford, S. A.Science of Synthesis, (200729965.

Glycosyl phosphorothioates may also be synthesized by anomeric S-phosphorylation (Scheme 43). Thus, sulfenyl bromide 135 (R1=Br) reacts with the nucleophilic H-phosphonate 136 (R2=H; X=O) in benzene (Method A) to give the phosphorothioate 137 (X=O) in a modest yield.[‌133‌] Alternatively, the glycosyl thiol 135 (R1=H) reacts under basic conditions (Method B, using NaOEt) with the phosphorochloridate 136 (R2=Cl; X=O) to give the same product.[‌133‌] This latter type of approach is the only route (Method C, using Et3N as the base) currently available for synthesizing the S-glycosyl phosphorothioselenoate 137 (X=Se) and related compounds free from their Se-glycosyl isomers.[‌134‌]

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