Full Text:   <1928>

CLC number: O621.3

On-line Access: 

Received: 2004-05-10

Revision Accepted: 2004-09-13

Crosschecked: 0000-00-00

Cited: 5

Clicked: 5294

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
1. Reference List
Open peer comments

Bio-Design and Manufacturing  2018 Vol.5 No.12 P.1509~1511

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)


Share this article to: More

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 D, 2018, 5(3): 1509~1511.

@article{title="Synthesis of arbutin by two-step reaction from glucose",
author="HUANG Shen-lin, ZHU Yu-lin, PAN Yuan-jiang, WU Shi-hua",
journal="Journal of Zhejiang University Science D",
volume="5",
number="12",
pages="1509~1511",
year="2018",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.1509"
}

%0 Journal Article
%T Synthesis of arbutin by two-step reaction from glucose
%A HUANG Shen-lin
%A ZHU Yu-lin
%A PAN Yuan-jiang
%A WU Shi-hua
%J Journal of Zhejiang University SCIENCE D
%V 5
%N 12
%P 1509~1511
%@ 1869-1951
%D 2018
%I Zhejiang University Press & Springer

TY - JOUR
T1 - Synthesis of arbutin by two-step reaction from glucose
A1 - HUANG Shen-lin
A1 - ZHU Yu-lin
A1 - PAN Yuan-jiang
A1 - WU Shi-hua
J0 - Journal of Zhejiang University Science D
VL - 5
IS - 12
SP - 1509
EP - 1511
%@ 1869-1951
Y1 - 2018
PB - Zhejiang University Press & Springer
ER -


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

[1] Bárczai-Martos, M., Kórösy, F., 1950. Preparation of Acetobrome-Sugars. Nature, 165:369.

[2] Chittenden, G.J.F., 1993. Reaction of some 1,2-trans-aldose peracetates with thionyl chloride-acetic acida convenient synthesis of some 1,2-trans-per-O-acetyl-D-glycosyl chlorides. Carbonhydr. Res., 242:297-301.

[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.

[4] Ernst, B., Winkler, T., 1989. Preparation of glycosyl halides under neutral conditions. Tetrahedron Lett., 30(23):3081-3084.

[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.

[6] Karjala, S., Link, K.P., 1940. Synthesis of glycol glucosides. J. Am. Chem. Soc., 62(4):917-920.

[7] Kartha, K.P.R., Jennings, H., 1990. A facile, one-step procedure for the conversion of 2-(trimethylsilyl) ethyl glycosides to their glycosyl chlorides. Tetrahedron Lett., 31(18):2537-2540.

[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.

[10] Lemeux, R.U., 1963. Methods in Carbohydrate Chemistry. Academic Press, New York, U.S.A., p.221.

[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.

[15] Pong, S.Q., Li, L.P., Wu, J.W., An, Y., Cheng, T.M., Cai, M.S., 1989. Synthesis of Arbutin Analogs. Acta Chimica Sinica, 47:512-515.

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

Please provide your name, email address and a comment





Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou 310027, China
Tel: +86-571-87952276/87952783; E-mail: jzus@zju.edu.cn
Copyright © 2000 - Journal of Zhejiang University-SCIENCE