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Journal of Zhejiang University SCIENCE A 2004 Vol.5 No.12 P.1509-1511

http://doi.org/10.1631/jzus.2004.1509


Synthesis of arbutin by two-step reaction from glucose


Author(s):  HUANG Shen-lin, ZHU Yu-lin, PAN Yuan-jiang, WU Shi-hua

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding email(s):   panyuanjiang@zju.edu.cn

Key Words:  Arbutin, Synthesis, 2, 3, 4, 6-tetra-O-acetyl-&alpha, -D-glucosyl halide (chloride or bromide), Acetyl halide (Cl, Br)


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HUANG Shen-lin, ZHU Yu-lin, PAN Yuan-jiang, WU Shi-hua. Synthesis of arbutin by two-step reaction from glucose[J]. Journal of Zhejiang University Science A, 2004, 5(12): 1509-1511.

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Abstract: 
4a8b>28arbutin%4a8b>29&ck%5B%5D=abstract&ck%5B%5D=keyword'>4a8b>2f4a8b>arbutin was synthesized from glucose by two-step reaction below: (a) 4a8b>2,4a8b>3,4,6-tetra-O-acetyl-&alpha;-D-glucosyl chloride or bromide was prepared by glucose and acetyl halide (chloride or bromide). (b) 4a8b>2,4a8b>3,4,6-tetra-O-acetyl-&alpha;-D-glucosyl halide (Cl, br) reacted with hydroquinone, methanol as solvent at pH=9.5~10.0.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

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[3] Cicchillo, R.M., Norris, P., 2000. A convenient synthesis of glycosyl chlorides from sugar hemiacetals using triphosgene as the chlorine source. Carbonhydr. Res., 328(3):431-434.

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[5] Hwang, C.K., Li, W.S., Nicolaou, K.C., 1984. Reactions of hydroxyl groups with tosylchloride-dimethylaminopyridine system. Direct synthesis of chlorides from hydroxycompounds. Tetrahedron Lett., 25(22):2295-2296.

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[8] Kovac, P., Edgar, K.J., 1992. Synthesis of ligands related to the O-specific antigen of type 1 Shigella dysenteriae. 3. Glycosylation of 4,6-O-substituted derivatives of methyl 2-acetamido-2-deoxy-.alpha.-D-glucopyranoside with glycosyl donors derived from mono- and oligosaccharides. J. Org. Chem., 57(8):2455-2467.

[9] Kovac, P., Taylor, R.B., Glaudemans, C.P.J., 1985. General synthesis of (1. fwdarw. 3)-.beta.-D-galacto oligosaccharides and their methyl .beta.-glycosides by a stepwise or a blockwise approach. J. Org. Chem., 50(25):5323-5333.

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[11] Mukherjee, D., Ray, P.K., Chowdhury, U.S., 2001. Synthesis of glycosides via indium(III) chloride mediated activation of glycosyl halide in neutral condition. Tetrahedron, 57(36):7701-7704.

[12] Ohrui, H., Fox, J.J., 1973. Nucleosides LXXXI. An approach to the synthesis of C-C linked β-D-ribofuranosyl nucleosides from 2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl chloride. Tetrahedron Lett., 14(22):1951-1954.

[13] Pacsu, E., 1928. Über die Einwirkung von Titan (IV)-chlorid auf Zucker-Derivate, I.: Neue Methode zur Darstellung der Aceto-chlor-zucker und Umlagerung des β-Methyl-glucosidsinseine α-Form. Ber., 61:1508-1513.

[14] Peromo, G.R., Krepinsky, J.J., 1987. A glycosylation reaction: Conversion of methyl glicosides to glycosyl chlorides by boron trichloride. Tetrahedron Lett., 28(46):5595-5598.

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Open peer comments: Debate/Discuss/Question/Opinion

<1>

Pierre@Lille<pierro_insomnia_005@hotmail.fr>

2014-11-18 17:27:12

phD student in organic chemistry

BIPIN@shah<dr.bpshah@vihita.com>

2014-07-27 14:49:18

Good paper
thank you
i am very happy

BIPIN@shah<dr.bpshah@vihita.com>

2014-07-27 14:46:51

good paper

dhassida@No address<dhassida\_t@yahoo.com>

2012-09-11 00:22:13

synthesis procedure

ezat@hussein<ezat_ahlam@yahoo.com>

2010-10-30 02:22:38

my name is ezat ,ihave ph.D in organic chemistry from baghdad university

waheed @in<waheedkhan@hotmail.co.in>

2010-10-21 20:00:07

reaction mechanism

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