Reaktion #501220

ord-ebc850133e3146a5ac194f0dd44c1b88

Reaktionsgleichung

O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
O=S(=O)(O)O
sulfuric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
D-sorbitol
COC[C@H](OC)[C@@H](OC)[C@H](O)[C@@H](COC)OC
1,2,3,5,6-penta-O-methyl-D-sorbitol
COC[C@@H](O)[C@@H](OC)[C@H](OC)[C@H](C=O)OC
2,3,4,6-tetra-O-methyl-D-glucose
→
OC[C@@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO
maltitol

Edukte

—
Sugar
—
( a )
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
O=S(=O)(O)O
sulfuric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
D-sorbitol
—
( b )
COC[C@H](OC)[C@@H](OC)[C@H](O)[C@@H](COC)OC
1,2,3,5,6-penta-O-methyl-D-sorbitol
COC[C@@H](O)[C@@H](OC)[C@H](OC)[C@H](C=O)OC
2,3,4,6-tetra-O-methyl-D-glucose

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige(c) The high specific rotation, [α]D20, of +106.5° and the infrared absorption

Vorschrift

Sugar components: (a) Acid hydrolysis using 1N sulfuric acid, and subsequent paper and gas-liquid chromatographic analyses confirmed the presence of equimolar D-glucose and D-sorbitol fractions; (b) Complete methylation, hydrolysis and subsequent gas-liquid chromatographic analysis confirmed the presence of equimolar 2,3,4,6-tetra-O-methyl-D-glucose and 1,2,3,5,6-penta-O-methyl-D-sorbitol fractions; (c) The high specific rotation, [α]D20, of +106.5° and the infrared absorption neighboring 840 cm-1 suggest the presence of an α-linkage between the glucose and sorbitol moieties; (d) Paper, gas-liquid and high-pressure liquid chromatographic analyses on the anhydrous crystals of maltitol gave the same single spot or peak at the same position as in the analyses on a commercial authentic maltitol preparation (special grade reagent).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04789559uspto-grants-1988_12