Réaction #2507804

ord-5460e37dfdd24cc7b64c8b2a1240bb3a

Équation de réaction

O=C(O)[C@H](O)[C@H](O)[C@H](O)CO
ribonic acid
O=C[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO
D-(+)-allose
O=C[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO
D-(+)-altrose
O=C(O)[C@@H](O)[C@H](O)[C@H](O)CO
D-arabinonic acid
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
→
O=C[C@H](O)[C@H](O)[C@H](O)CO
D-(−)-ribose

Réactifs

O=C(O)[C@H](O)[C@H](O)[C@H](O)CO
ribonic acid
O=C[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO
D-(+)-allose
—
sugar
O=C[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO
D-(+)-altrose
O=C(O)[C@@H](O)[C@H](O)[C@H](O)CO
D-arabinonic acid
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
—
reactant 90

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrea decarboxylation reaction 35

Mode opératoire

In another aspect of the second embodiment, D-arabinonic acid reactant 90 may be prepared by decarboxylation 80 of a D-glucose starting material 60 by one or more reactions. Referring to FIG. 2, the starting material can be converted to an arabinonic reactant 90 or a ribonic acid reactant 40 by one or more reaction steps. Preferably, a suitable C-6 sugar starting material is decarboxylated at the C-1 position. Optionally, a starting material comprising D-(+)-allose or D-(+)-altrose can undergo a decarboxylation reaction 35 to produce an intermediate comprising D-(−)-ribose (aldehyde) that can subsequently undergo an oxidation reaction 37 to produce the desired reactant 40 comprising D-ribonic acid. Similarly, a starting material comprising D-(+)-glucose or D-(+)-mannose can undergo a decarboxylation reaction 85 to produce an intermediate comprising D-(−)-arabinose (aldehyde) that can subsequently undergo an oxidation reaction 87 to produce the desired reactant 90 comprising D-arabinonic acid. U.S. Pat. No. 4,515,667 describes a process for the photochemical decarboxylation of an alpha-hydroxy carboxylic acid to the corresponding alcohol which process comprises irradiating a mixture of a solution of an alpha-hydroxy carboxylic acid and a metal titanate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07955489B2uspto-grants-2011_06