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Molecules 2014, 19(5), 6683-6693; doi:10.3390/molecules19056683
Article

Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides

, , , , *  and
Received: 31 March 2014; in revised form: 9 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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Abstract: A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of α-D-mannopyranosides is reported. Treatment of various α-D-mannopyranosides with 0.12 equiv of the TsOH·H2O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-D-mannopyranosides directly in 80%~90% yields. Based on this method, a 3,6-branched α-D-mannosyl trisaccharide was prepared in 50.4% total yield using p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside as the starting material.
Keywords: 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Jiang, R.; Zong, G.; Liang, X.; Jin, S.; Zhang, J.; Wang, D. Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides. Molecules 2014, 19, 6683-6693.

AMA Style

Jiang R, Zong G, Liang X, Jin S, Zhang J, Wang D. Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides. Molecules. 2014; 19(5):6683-6693.

Chicago/Turabian Style

Jiang, Rui; Zong, Guanghui; Liang, Xiaomei; Jin, Shuhui; Zhang, Jianjun; Wang, Daoquan. 2014. "Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides." Molecules 19, no. 5: 6683-6693.


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