Stereoselective Dihydroxylation Reaction of Alkenyl ß-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-ß-D-glycosyl-sn-glycerol Analogues

被引：7

作者：

Vega-Perez, Jose M. ^{[1
]}

Palo-Nieto, Carlos ^{[1
]}

Perinan, Ignacio ^{[1
]}

Vega-Holm, Margarita ^{[1
]}

Calderon-Montano, Jose M. ^{[2
]}

Lopez-Lazaro, Miguel ^{[2
]}

Iglesias-Guerra, Fernando ^{[1
]}

机构：

[1] Univ Seville, Dept Quim Organ & Farmaceut, Fac Farm, Seville 41012, Spain

[2] Univ Seville, Dept Farmacol, Fac Farm, Seville, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 06期

关键词：

Synthetic methods; Asymmetric synthesis; Carbohydrates; Diastereo-selectivity; Biological activity; Dihydroxylation; POTENTIAL ANTICANCER DRUGS; TUMOR-PROMOTING ACTIVITY; ALLYLIC ALCOHOL SYSTEMS; ALKYLATING-AGENTS; ASYMMETRIC DIHYDROXYLATION; GLYCOGLYCEROLIPID ANALOGS; OSMIUM-TETROXIDE; NATURAL-PRODUCT; D-GLUCOSAMINE; D-GLUCO;

D O I：

10.1002/ejoc.201101539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl beta-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group (OH, NHAc) at the 2-position of the sugar moiety is required to obtain high levels of stereofacial discrimination. New 1-O-acyl-3-O-beta-D-glycosyl-sn-glycerol analogues were obtained by functionalisation of the primary hydroxy group with a fatty acid. Preliminary cytotoxic activity assays of both glycosylglycerol and glycoglycerolipid analogues are also presented.

引用

页码：1237 / 1252

页数：16

共 55 条

[1] An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-beta-D-glucosylglycerol ethers by epoxidation of an allyl beta-D-glucopyranoside asymmetrically induced by the glucide moiety [J].

Bellucci, G ;

Catelani, G ;

Chiappe, C ;

DAndrea, F ;

Grigo, G .

TETRAHEDRON-ASYMMETRY, 1997, 8 (05) :765-773

[2] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[3] ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].

CHA, JK ;

KIM, NS .

CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795

[4] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON LETTERS, 1983, 24 (37) :3943-3946

[5] Total synthesis of eudesmane terpenes by site-selective C-H oxidations [J].

Chen, Ke ;

Baran, Phil S. .

NATURE, 2009, 459 (7248) :824-828

[6]

Christie S.D. R., 2008, SYNTHESIS, V9, P1325

[7] MECHANISM OF FORMATION OF BIS(PYRIDINE)OXOOSMIUM(VI) ESTERS - EFFECT OF PYRIDINE ACTIVITY ON APPARENT RATE LAW [J].

CLARK, RL ;

BEHRMAN, EJ .

INORGANIC CHEMISTRY, 1975, 14 (06) :1425-1426

[8] Glycoglycerolipid analogues active as anti-tumor-promoters: the influence of the anomeric configuration [J].

Colombo, D ;

Compostella, F ;

Ronchetti, F ;

Scala, A ;

Toma, L ;

Tokuda, H ;

Nishino, H .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (12) :1109-1113

[9] Bioctive glycoglycerolipid analogues:: an expeditious enzymatic approach to mono- and diesters of 2-O-β-D-galactoglycerol [J].

Colombo, D ;

Ronchetti, F ;

Scala, A ;

Toma, L .

TETRAHEDRON-ASYMMETRY, 1998, 9 (12) :2113-2119

[10]

Compostella F, 2002, EUR J ORG CHEM, V2002, P1429

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