The Preparation and Proof of Structure of 1,2:5,6-Dicyclohexylidene-D-glucofuranose

Hockett, Robert C.; Miller, R. E.; Scattergood, Allen

doi:10.1021/ja01177a036

Cited by 35 publications

(6 citation statements)

References 2 publications

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“…2 − 5 were synthesized in good yields by a procedure similar to that used for 1 . 1,2:5,6-di- O -cyclohexylidene-α- d -glucofuranose, 1,2:3,4-di- O -isopropylidene-α- d -galactopyranose, 1,2:4,5-Di- O -isopropylidene-β- d -fructopyranose, or 2,3:4,6-di- O -isopropylidene-β- l -sorbofuranose was used in each of the reactions. After the usual workup, flash column chromatography on silica gel (hexanes/EtOAc, 8.5/1.5 v/v) afforded 2 , 3 , or 4 as a colorless syrup or 5 as a white solid with a low melting point near room temperature (ca.…”

Section: Methodsmentioning

confidence: 99%

Protection and Polymerization of Functional Monomers. 28. Anionic Living Polymerization of Styrene Derivatives Containing Acetal-Protected Monosaccharide Residues

1998

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Six styrene derivatives meta-substituted with acetal-protected glucofuranoses (1) and (2), galactopyranose (3), fructopyranose (4), and sorbofuranose (5) and para-substituted with acetal-protected glucofuranose (6) were synthesized by the Williamson reactions of m- or p-(chloromethyl)styrene with the corresponding protected monosaccharides in DMF and were anionically polymerized. The anionic polymerizations were carried out with s-BuLi in THF at −78 °C for 30 min. Among the monomers, 1−5, were found to undergo anionic living polymerization to afford quantitatively the polymers of predictable molecular weights and narrow molecular weight distributions (M w/M n < 1.13). Novel well-defined block copolymers, polystyrene-block-poly(1) starting either from living polystyrene or the living polymer of 1, were successfully synthesized. By contrast, no appreciable polymerization of 6 occurred under identical conditions.

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Section: Methodsmentioning

confidence: 99%

Protection and Polymerization of Functional Monomers. 28. Anionic Living Polymerization of Styrene Derivatives Containing Acetal-Protected Monosaccharide Residues

1998

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“…In view of the ready accessibility of many bridgehead carboxylic acids, particularly highly constrained systems via a Favorskii-type ring contraction,10 we set out to develop a general route to bridgehead iodides using the carboxylic acids [1][2][3][4][5][6] (R = COOH) as typical substrates.…”

Section: Methodsmentioning

confidence: 99%

“…J. Org.Chem. 1967, 32, 31 and earlier papers cited therein (6). Lansbury, P. T.; Pattison, V. A.; Sidler, J. D.; Bieber, J.…”

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confidence: 97%

Decarboxylative iodination: a convenient synthesis of bridgehead iodides

Abeywickrema¹,

Della²

1980

J. Org. Chem.

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“…Methylene acetals appear to be more resistant to hydrolysis than their higher homologues (1). Cylic acetals containing fused five-membered rings such as 1,2-0-isopropylidene-D-glucofuranose (5) and 1,2-0-cyclohexylidene-D-glucofuranose (6) have been shown to be relatively resistant to acid hydrolysis.…”

Section: Chemistry Of Acetalsmentioning

confidence: 99%

“…The liquid phase from which they finally isolated the compound had water added to it. This water, along with the zinc chloride present could constitute the conditions of a mild hydrolysis; conditions under which fused five-membered rings are relatively stable(5)(6)(7).,. This rela--.tive stability toward hydrolysis was confirmed in this work by the fact that 1.,2-benzylidene glucose would not react with the acidified p-anisidine spray reagent, but the 1,2:4,6-dibenzylidene glucose would.…”

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confidence: 99%