Acetic Anhydride → 1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

HRID 25469

Reaction equation

CS(C)=O.C(OC(=O)C)(=O)C.[CH3:12][C:13]1([CH3:29])[O:17][C@@H:16]([C@H:18]2[O:22][C@@H:21]3[O:23][C:24]([CH3:27])([CH3:26])[O:25][C@@H:20]3[C@H:19]2[OH:28])[CH2:15][O:14]1.C(OC(=O)C)(=O)C>>[CH3:12][C:13]1([CH3:29])[O:17][C@@H:16]([C@H:18]2[O:22][C@@H:21]3[O:23][C:24]([CH3:27])([CH3:26])[O:25][C@@H:20]3[C@@H:19]2[OH:28])[CH2:15][O:14]1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 7067560Diacetone-D-glucose

HCID 86609981DMSO acetic anhydride

Product 1

HCID 71570541,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

Procedure

Sowa, W. and Thomas, G. H. S., (Can. J. of Chem., 1966, Vol. 44, 836-838) used the DMSO/acetic anhydride oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose in small scale (10 mmole) using a 20 fold excess of acetic anhydride. The ulose was then reduced providing 1,2:5,6-di-O-isopropylidene-α-D-allofuranose of poor quality, thus the product had to be column purified. Overall this procedure is not suitable for large-scale productions due to the large reagent consumption, two step procedure and the column purification step.

Sources & evidence

ORD record: ord-a62ddce00f3040878d58f6747e85353c
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858726B2

Linked notes

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