5-Thiopyranoses. Part 11. Isopropylidene acetals of 5-thio-D-glucose, 5-thio-D-allose, and 5-thio-D-altrose and some of their methyl glycosides

Al‐Masoudi, Najim A.; Hughes, N. A.

doi:10.1039/p19870001413

J. Chem. Soc., Perkin Trans. 1

1987

DOI: 10.1039/p19870001413

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5-Thiopyranoses. Part 11. Isopropylidene acetals of 5-thio-D-glucose, 5-thio-D-allose, and 5-thio-D-altrose and some of their methyl glycosides

Najim A. Al‐Masoudi¹,

N. A. Hughes²

Abstract: The thioglucose (I) or the thioaltrose (VII) react with acetone (III) in the presence of an acid to give the products (II) or (VIII) whereas the diacetal (XI) is obtained from the thioallose (IX).

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Cited by 8 publications

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ChemInform Abstract: 5‐Thiopyranoses. Part 11. Isopropylidene Acetals of 5‐Thio‐D‐glucose, 5‐Thio‐D‐allose, and 5‐Thio‐D‐altrose and Some of Their Methyl Glycosides.

Al‐Masoudi¹,

Hughes²

1987

ChemInform

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340ChemInform Abstract The thioglucose (I) or the thioaltrose (VII) react with acetone (III) in the presence of an acid to give the products (II) or (VIII) whereas the diacetal (XI) is obtained from the thioallose (IX). Under kinetic conditions, using (III) and added dimethoxypropane (IV), the major products from (I) are the compounds (V) and (VI). The thioaltropyranoside (XII) reacts with (III) to form the kinetic product (XIII) which isomerizes into the acetal (XIV). A mixture of the monoacetal (XVIa) and the diacetal (XVIb) is obtained from the α-glucopyranoside (XV) with acetone (III) while (XVIb) is the sole product when (XV) reacts with (III) + (IV). The β-anomer of (XV) behaves analogously. Methylation of (V) or (XI) leads to the aldehydes (XVII) or (XVIII).

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ChemInform Abstract: 5‐Thiopyranoses. Part 11. Isopropylidene Acetals of 5‐Thio‐D‐glucose, 5‐Thio‐D‐allose, and 5‐Thio‐D‐altrose and Some of Their Methyl Glycosides.

Al‐Masoudi¹,

Hughes²

1987

ChemInform

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Synthesis of derivatives of 5-thio- l -idose

Hughes

Munkombwe

Todhunter

1992

Carbohydrate Research

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The reaction of methyl 5-thio-3-O-toluene-p-sulfonyl-α-d-glucopyranoside and its triacetate with sodium azide

Al‐Masoudi

Pfleiderer

1993

Carbohydrate Research

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5-Thiopyranoses. Part 11. Isopropylidene acetals of 5-thio-D-glucose, 5-thio-D-allose, and 5-thio-D-altrose and some of their methyl glycosides

Abstract: The thioglucose (I) or the thioaltrose (VII) react with acetone (III) in the presence of an acid to give the products (II) or (VIII) whereas the diacetal (XI) is obtained from the thioallose (IX).

Cited by 8 publications

References 7 publications

ChemInform Abstract: 5‐Thiopyranoses. Part 11. Isopropylidene Acetals of 5‐Thio‐D‐glucose, 5‐Thio‐D‐allose, and 5‐Thio‐D‐altrose and Some of Their Methyl Glycosides.

ChemInform Abstract: 5‐Thiopyranoses. Part 11. Isopropylidene Acetals of 5‐Thio‐D‐glucose, 5‐Thio‐D‐allose, and 5‐Thio‐D‐altrose and Some of Their Methyl Glycosides.

Synthesis of derivatives of 5-thio- l -idose

The reaction of methyl 5-thio-3-O-toluene-p-sulfonyl-α-d-glucopyranoside and its triacetate with sodium azide

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