Thio-P-D-mannopyranosides

4-Nitrophenyl l-thio-P-o-mannopyranoside has been synthesized by reaction of acetochloromannose [207] or the mannosyl bromide 2 [202] with the sodium salt of 4-nitrothiophenol. A similar reaction between sodium thiophenoxide and aceto-bromomannose in HMPT gives phenyl 1-thio-P-D-mannopyranoside quantitatively [208]. In a related reaction the sodium salt of 1-thio-P-D-mannopyranose has been alkylated with benzyl bromide as in Schmidt s approach (Section 13.2.4) to give benzyl P-thiomannoside in 86% yield [209]. P-Linked 1-thiomannopyranosides can also be prepared by BFs-catalyzed anomerization of the readily available a-anomers [46]. The Lindberg protocol has also been used for the synthesis 1-thio-P-D-mannopyranosides [146, 149]. Aryl 1-thio-p-mannofuranosides have been syn- 

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Et glycoside, tetra-Ac Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-p-D-mannopyranoside [125354-48-5]... 

Ph glycoside, di-O-isopropylidene Phenyl 2,3 4,6-di-0-isopropyliderK-l-thio-P-D-mannopyranoside [151662-55-4]... 

Penta-0-acetyl-5-thio-o -D-mannopyranose, T-85 l-5,2,3,4,6-Pentaacetyl-l-thio-p-D-mannopyranoside, T-82 Penta-O -benzoyl-(+)-ej j -inosose, 1-35... 

Phenyl 4-0-benzyI-l-thio-a-D-rhamnopyranoside, T-S6 Phenyl 4,6-di-O-acetyI-l-thio-p-D-mannopyranoside, T-82 Phenyl 2,3 4,6-di-0-isopropyIidene-l-thio-p-D-mannopyranoside, T-S2 Phenyl 3,4-O-isopropyIidene-l-thio-p-D-galactopyranoside, T-65 Phenyl 2,3-O-isopropyIidene-l-thio-a-D-rhamnopyranoside, T-86 Phenyl 2,3-O-isopropyIidene-l-thio-a-L-rhamnopyranosid T-86 Phenyl 2,3-0-isopropyIidene-l-thio-6-0-tosyI-a-i>mannopyranoside,... 

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