Directed and undirected asymmetric dihydroxylation reactions:: application in the synthesis of a C-linked analogue of allolactose

被引：12

作者：

Hodgson, R

Mahid, T

Nelson, A ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] Aventis Pharma US, Bridgewater, NJ 08807 USA

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 20期

关键词：

D O I：

10.1039/b107643d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The complex OsO4. (S,S)-1,2-diphenyl-N,N'-bis(2,4,6-trimethylbenzyl)ethane-1,2-diamine is an effective reagent for the desymmetrisation of meso-1,2-bis(3,6-dihydro-2H-pyran-2-yl)ethanes by asymmetric dihydroxylation; this process, whose sense of diastereoselectivity depends on substitution and stereochemistry, has been exploited in the synthesis of a C-linked analogue of allolactose.

引用

收藏

页码：2076 / 2077

页数：2

相关论文

共 17 条

[1] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].

BEHRENS, CH ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704

[2] SYNTHESIS OF ALPHA-(1-]2)-, ALPHA-(1-]3)-, ALPHA-(1-]4)-, AND ALPHA-(1-]5)-C-LINKED DISACCHARIDES THROUGH 2,3,4,6-TETRA-O-ACETYLGLUCOPYRANOSYL RADICAL ADDITIONS TO 3-METHYLIDENE-7-OXABICYCLO[2.2.1]HEPTAN-2-ONE DERIVATIVES [J].

BIMWALA, RM ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2076-2083

[3] 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

[4] Synthesis of alpha- and beta-D-(1->-6)-C-disaccharides by Wittig olefination of formyl C-glycosides with glycopyranose 6-phosphoranes [J].

Dondoni, A ;

Zuurmond, HM ;

Boscarato, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8114-8124

[5] The directed dihydroxylation of allylic alcohols [J].

Donohoe, TJ ;

Moore, PR ;

Waring, MJ ;

Newcombe, NJ .

TETRAHEDRON LETTERS, 1997, 38 (28) :5027-5030

[6] NAKED SUGARS AS SYNTHETIC INTERMEDIATES .26. SYNTHESIS OF ALPHA-D-(1-]3) AND ALPHA-D-(1-]4)-C-LINKED GALACTOSIDES OF D-MANNOSE DERIVATIVES - CONFORMATION OF ALPHA-C-GALACTOSIDES [J].

FERRITTO, R ;

VOGEL, P .

TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2077-2092

[7] First synthesis of (±)-1α,2α,4β-trihydroxycyclohex-5-ene.: Anchimeric assistance in conduritol syntheses. [J].

Haines, AH ;

King, ASH ;

Knight, JR ;

Nguyen, VA .

TETRAHEDRON LETTERS, 1998, 39 (24) :4393-4396

[8] A general, two-directional synthesis of C-(1→6)-linked disaccharide mimetics:: synthesis from non-carbohydrate based starting materials [J].

Harding, M ;

Nelson, A .

CHEMICAL COMMUNICATIONS, 2001, (08) :695-696

[9] SYNTHESIS OF OPTICALLY-ACTIVE 2-FURYLMETHANOLS AS USEFUL CHIRAL BUILDING-BLOCKS AND ITS APPLICATION TO THE SYNTHESIS OF (5R,6S)-6-ACETOXYHEXADECAN-5-OLIDE AND (+)-DISPARLURE [J].

KAMETANI, T ;

TSUBUKI, M ;

TATSUZAKI, Y ;

HONDA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :639-646

[10] C-glycosyl aldehydes: Synthons for C-linked disaccharides [J].

Kobertz, WR ;

Bertozzi, CR ;

Bednarski, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1894-1897