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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 6
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Original Articles

Synthesis of a Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its 2‐(Trimethylsilyl)ethyl Glycoside

Samarpita Roy Department of Biological Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700 032, India
,
Sujit Kumar Sarkar Department of Biological Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700 032, India
&
Nirmolendu Roy Department of Biological Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700 032, IndiaCorrespondence[email protected] [email protected]
Pages 1125-1139 | Received 08 Sep 2003, Published online: 21 Aug 2006
 
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Abstract

Starting from D‐mannose, D‐galactose and D‐glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique for trichloroacetimidate was utilized for the construction of a disaccharide with a β‐mannosidic linkage in good yield. The two disaccharides in the appropriate form were then allowed to react in the presence of N‐iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the tetrasaccharide derivative from which removal of protecting groups gave the desired tetrasaccharide in the form of its 2‐(trimethylsilyl)ethyl glycoside.

Acknowledgment

Financial support from the Department of Science and Technology, New Delhi, India (Project No. SP/S1/G14/95) is thankfully acknowledged.

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