Journal of the American Chemical Society

The Synthesis of the Four Possible Methyl 3-Amino-3-deoxy-D-xylosides. A Novel Ring Expansion of a Furanoside to a Pyranoside

RE Schaub, MJ Weiss

Index: Schaub; Weiss Journal of the American Chemical Society, 1958 , vol. 80, p. 4683,4689

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Citation Number: 35

Abstract

Consumption by A of 2.0 equivalents of periodate within five minutes indicated a pyranoside config~ rati0n. l~ This, coupled with the failure of the N-acetyl derivative of A to consume any periodate, required an amino group at C-3 and, therefore, A was considered to be a methyl 3- amino-3-deoxypentopyranoside. More specifically, it was postulated that A was a 3- aminoxylopyranoside for the following reasons. The formation of a pyranoside from ...