2-β-d-ribofuranosylbenzoxazole from 2,5-anhydro-d-allonoimidate, and 1,3-dimethyl-8-β-d-ribofuranosylxanthine from 2,5-anhydro-d-allono-thioimidates and -dithioates

Khadem, Hassan S. El; Kawai, J.

doi:10.1016/s0008-6215(00)90269-6

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1987

2004

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Cited by 15 publications

(1 citation statement)

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“…In this regard, they have served as important intermediates in the synthesis of a wide variety of sugar derivatives such as C -glycosyl α-glycines, cyclopeptides containing a sugar amino acid moiety, C -nucleoside derivatives, and C -glycoside heterocycles. − …”

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confidence: 99%

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

2004

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[reaction: see text] An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such S(N)2-type displacements at the anomeric center are stereospecific and are best performed with sodium cyanide in the presence of ytterbium triflate. Significantly, the resulting 1,2-trans-glycosyl cyanides have a free hydroxyl group at C-2 ready for further modification.

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confidence: 99%

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

2004

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Imidates including cyclic imidates

Neilson

1991

PATAI'S Chemistry of Functional Groups

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ChemInform Abstract: 2‐β‐D‐Ribofuranosylbenzoxazole from 2,5‐Anhydro‐D‐allonoimidate, and 1,3‐Dimethyl‐8‐β‐D‐ribofuranosylxanthine from 2,5‐Anhydro‐D‐allono‐ thioimidates and ‐dithioates.

Khadem

Kawai

1987

ChemInform

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353ChemInform Abstract The reaction between the imidates (I) and the aminophenol (II) yields the benzoxazole (III) only. The trimethylxanthine (VII) can be prepared by reacting (Ia) with (IV) via the intermediate (V) or by cyclization of the dithioester (VI) with (IV). The carbohydrate derivatives (X) and (XI), prepared by the Pinner procedure, are converted to the corresponding derivatives (XII) -(XV) in a similar manner. Aromatization of the furanose ring takes place in the reaction of (Xd) and (Xf) with (IV) to produce (XIII). (IR-and 1H-NMR-data).

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2-β-d-ribofuranosylbenzoxazole from 2,5-anhydro-d-allonoimidate, and 1,3-dimethyl-8-β-d-ribofuranosylxanthine from 2,5-anhydro-d-allono-thioimidates and -dithioates

Cited by 15 publications

References 20 publications

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

Imidates including cyclic imidates

ChemInform Abstract: 2‐β‐D‐Ribofuranosylbenzoxazole from 2,5‐Anhydro‐D‐allonoimidate, and 1,3‐Dimethyl‐8‐β‐D‐ribofuranosylxanthine from 2,5‐Anhydro‐D‐allono‐ thioimidates and ‐dithioates.

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