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Citation: LI Gen, QIAN Zhao-Sheng, CAO Ling-Hua. The Oxidation of Primary Hydroxyl Group of Galactose and the Synthesis of Its Derivatives[J]. Chinese Journal of Applied Chemistry, ;2005, 22(11): 1182-1186. shu

The Oxidation of Primary Hydroxyl Group of Galactose and the Synthesis of Its Derivatives

1.
a College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046;
2.
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Corresponding author: CAO Ling-Hua,
Received Date: 22 November 2004
Available Online: 14 May 2005
Fund Project: 国家自然科学基金(2996200220462006)资助项目 (2996200220462006)

By the oxidation of primary hydroxyl group of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(1),1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose(2) was prepared.By reaction of compound 2 with hydrazines or hydrazides,a series of 1,2:3,4-di-O-isopropylidene-α-D-galacto-(hexodialdo-)1,5-pyranose(heterocyclyl or aryl) substituted carbonyl hydrazone(3a~3f) and 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose substituted aryl hydrazone(4a,4b) were prepared.By nucleophilic addition reaction of compound 1 with glycosyl isothiocyanates,a series of new compounds 6-O-[N-(2,3,4,6-tetra-O-acetyl-glycosyl) thiocarbamoyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(5a~5e) were prepared.The structures of all the compounds were established by IR,¹H NMR and elemental analysis.
- D-galactose,
- oxidation,
- glycosyl isothiocyanate,
- nucleophilic addition
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