Sulfuric Acid → Maltitol

HRID 414038Notes

Reaction equation

S(=O)(=O)(O)O.[O:6]=[CH:7][C@@H:8]([C@H:10]([C@@H:12]([C@@H:14]([CH2:16][OH:17])[OH:15])[OH:13])[OH:11])[OH:9].[OH:18][CH2:19][C@@H:20]([C@H:22]([C@@H:24]([C@@H:26]([CH2:28][OH:29])[OH:27])O)[OH:23])[OH:21].CO[C@H]([C@H]([C@@H]([C@@H](COC)O)OC)OC)C=O.COC[C@@H]([C@H]([C@@H]([C@@H](COC)OC)O)OC)OC>>[CH2:16]([OH:17])[C@H:14]1[O:15][C@H:7]([O:6][C@@H:24]([C@H:22]([OH:23])[C@@H:20]([OH:21])[CH2:19][OH:18])[C@H:26]([OH:27])[CH2:28][OH:29])[C@H:8]([OH:9])[C@@H:10]([OH:11])[C@@H:12]1[OH:13]

Participants

Reactant 5

HCID 1118Sulfuric Acid

HCID 5780Sorbitol

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HCID 141043352,3,4,6-Tetra-O-methyl-D-glucose

HCID 15689262HCID 15689262, compound

Product 1

HCID 493591Maltitol

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ebc850133e3146a5ac194f0dd44c1b88
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04789559

Reaction notes

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