An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

被引：83

作者：

Fulton, DA ^{[1
]}

Stoddart, JF ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 08期

关键词：

D O I：

10.1021/ol005668x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-beta-D-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6 diallyl-beta-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of beta-cyclodextrin-not to mention (3) both the primary and secondary faces, simultaneously-in yields of up to 70%.

引用

页码：1113 / 1116

页数：4

共 42 条

[1] A QCM study on adsorption of macrocyclic sugar-cluster to variously-functionalized monolayers [J].

Ariga, K ;

Isoyama, K ;

Hayashida, O ;

Aoyama, Y ;

Okahata, Y .

CHEMISTRY LETTERS, 1998, (10) :1007-1008

[2] Synthesis and biological evaluation of α-D-mannopyranoside-containing dendrimers [J].

Ashton, PR ;

Hounsell, EF ;

Jayaraman, N ;

Nilsen, TM ;

Spencer, N ;

Stoddart, JF ;

Young, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3429-3437

[3] RECOGNITION ABILITY AND CYTOTOXICITY OF SOME OLIGOSACCHARIDYL SUBSTITUTED BETA-CYCLODEXTRINS [J].

ATTIOUI, F ;

ALOMAR, A ;

LERAY, E ;

PARROTLOPEZ, H ;

FINANCE, C ;

BONALY, R .

BIOLOGY OF THE CELL, 1994, 82 (2-3) :161-167

[4] SELECTIVE ALKYLATION OF CYCLOHEPTAAMYLOSE [J].

BERGERON, RJ ;

MEELEY, MP ;

MACHIDA, Y .

BIOORGANIC CHEMISTRY, 1976, 5 (01) :121-126

[5] On the meaning of affinity: Cluster glycoside effects and concanavalin A [J].

Dimick, SM ;

Powell, SC ;

McMahon, SA ;

Moothoo, DN ;

Naismith, JH ;

Toone, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10286-10296

[6] Synthesis and properties of O-glycosyl calix[4]arenes (calixsugars) [J].

Dondoni, A ;

Marra, A ;

Scherrmann, MC ;

Casnati, A ;

Sansone, F ;

Ungaro, R .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (11) :1774-1782

[7] The assembly of carbon-linked calixarene-carbohydrate structures (C-calixsugars) by multiple Wittig olefination [J].

Dondoni, A ;

Kleban, M ;

Marra, A .

TETRAHEDRON LETTERS, 1997, 38 (44) :7801-7804

[8]

FERNANDEZ JMG, 1996, J CHEM SOC CHEM COMM, P2741

[9] Solution-to-surface molecular-delivery system using a macrocyclic sugar cluster. Sugar-directed adsorption of guests in water on polar solid surfaces [J].

Fujimoto, T ;

Shimizu, C ;

Hayashida, O ;

Aoyama, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) :6676-6677

[10] Ternary complexation involving protein. Molecular transport to saccharide-binding proteins using macrocyclic saccharide cluster as specific transporter [J].

Fujimoto, T ;

Shimizu, C ;

Hayashida, O ;

Aoyama, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (03) :601-602

← 1 2 3 4 5 →