Optimized Procedure for the Synthesis of 6‐Azido‐6‐deoxy‐galactopyranosides From 6‐<i>O</i>‐Tosyl‐galactopyranosides

Li, Shu‐Chun; Meng, Xiangbao; Cai, Meng‐Shen; Li, Zhongjun

doi:10.1080/00397910500408787

Cited by 8 publications

(2 citation statements)

References 18 publications

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“…The reaction of sucrose with 1.1 eq. of the bulky reagent tert-butyldiphenylsilyl chloride (TBDPSCl) led to the sole protect of the hydroxyl group at position 6 of the fructose moiety by yield 6'-O-tert-butyldiphenylsilyl sucrose (2) [10][11][12] . Afterword remaining hydroxyl groups can be easily acylated with acetic anhydride in pyridine to form the fully protected sucrose compounds 1',2,3,3',4,4',6-hepta-O-acetyl-6'-tertbutyldiphenylsilyl-sucrose (3) 13 .…”

Section: Synthesismentioning

confidence: 99%

Straight and Branched Sucrose Monoamide Derivatives as New Surfactants

2016

Chem Sci Trans

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Abstract:We have synthesized monoamide analogs of sucrose. The synthesis applied a multi steps synthesis scheme ended by Staudinger reaction based coupling of a sucrose azide with fatty acid chlorides. Sucrose monoamide surfactants are easily accessible surfactants from sucrose, which is consider as the cheapest natural carbohydrate resources. The assembly behavior of synthesized monoamide derivatives was investigated by optical polarizing microscopy, Differential scanning calorimetry DSC and surface tension studies. These surfactants exhibit very good solubility in water at room temperature and value of CMC within the range of disaccharides surfactants, which make those surfactants fitting the target application as water-in-oil emulsions.

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Section: Synthesismentioning

confidence: 99%

Straight and Branched Sucrose Monoamide Derivatives as New Surfactants

2016

Chem Sci Trans

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“…The modified method of Kondo et al (19) was used to tosylate the C-6 of glucose. Then, a substitution of tosyl by an azide group was realized using the modified methods of Brimakombe et al (14) and Li et al (20), and azide reduction was followed using the modified method of Jary et al (15). To synthesize 6-(p-toluenesulfonyl)-R-D-methylglucoside, R-D-methylglucoside (10 g, 51.5 mmol) was dissolved in 20 mL of pyridine previously dried on 4A molecular sieves.…”

Section: Chemicalsmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Aminodeoxyglucose Derivatives against Listeria innocua and Salmonella typhimurium

Muhizi¹,

Grelier²,

Coma³

2009

J. Agric. Food Chem.

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In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium . 6-Amino-6-deoxy-alpha-D-methylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and beta-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 x 10(-4) mol mL(-1), it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, (1)H NMR, and (13)C NMR spectroscopy.

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