3-D-glucopyranosides

Benzyl-2-acetamido-4,6-(7-benzylidene-2-deoxy-a-D-glucopyranoside [13343-63-0] M 399.4, m 256-261 , 263-264 , [alp +120 (c 1, pyridine). Wash with cold isoPrOH and crystallise from dioxane/isoPrOH. [/ Org Chem 32 2759 1967.]... 

Picein (p-acetylphenyl-p-D-glucopyranoside) [530-14-3] 1, H2O). Crystd from MeOH or (as monohydrate) from water. 

Cyclic sulfates rapidly react with the fluoride ion sources to give monofluoro derivatives Thus, the 2,3-cyclic sulfate of methyl-4 6 O benzylidene p D manno pyranoside cleanly reacts with tetramethylammonium fluoride to give methyl 4,6-0-benzylidene 2 deoxy 2 fluoro-p-D-glucopyranoside-3-sulfate Acid hydrolysis followed by acetylation gives 2 deoxy 2 fluoro-P-D-glucopyranoside triacetate in 84% isolated yield [5S] (equation 38)... 

The reaction of the sodium salts of pyrido[2,3-e]-l,2,4-triazin-3(4//)-one 1-oxide 22 (Y = N) or l,2,4-benzotriazin-3(4//)-one 1-oxide 23 with acetobro-moglucose results in tetra-(9-acetyl derivatives of /3-D-glucopyranosides 24, 25 deacetylation of 25 gives nucleosides 26 (82JHC497). 

Chemical Name S-Triethylphosphinagold 2,3,4,6-tetra-0-acetyl-1-thio-/3-D-glucopyranoside Common Name —... 

Chemical Name Hexadeca-)U-hydroxytetracosahydroxyl/Ug-l 1,3,4,6-tetra-O-suifo-/3-D-fructo-furanosyl-a-D-glucopyranoside tetrakisihydrogen sulfato)(8-)] ] hexadecaaluminum... 

Our initial studies were directed towards the synthesis and characterization of phenylboronate esters derived from methyl 6-deoxy-/ -D-allopyranoside, methyl a-L-rhamnopyranoside, methyl -L-fucopyranoside, and methyl 6-deoxy-/ -D-glucopyranoside. Previous work (14) in this laboratory indicated that the reaction of triphenylboroxole and methyl... 

A mixture of d- and l- hexoses also results from the hydroboration of these 5-enes. Hydroboration results in anti-Markownikoff, cw-hydration of the double bond and the amount of each hexose formed varies according to the nature of the substituent groups. For example, hydroboration (23) of methyl 6-deoxy-a-D-ryZo-hex-5-enopyranose (3) affords methyl a-D-glucopyranoside and methyl / -L-idopyranoside in the ratio of 1 2.5 respectively whereas hydroboration of the fris-trimethylsilyl ether of 3 afforded them in the ratio 1 0.6 respectively. The hydroboration method can be used to achieve specific labelling of hexoses with tritium methyl-/ -L-idopyranoside[5-H3] and methyl a-D-glucopyranoside [5-H3] were thus prepared (23). Similarly, hydroboration of the D-Zt/ro-hex-5-eno derivative (14) with diborane-H3 followed by removal of the isopropyli-dene group, afforded methyl a-D-mannopyranoside [5-H3] and methyl / -L-gulopyranoside [5-H3] in the ratio of 1 2 respectively (23). 

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