Aryl and arylmethyl C-glycosides through desulfitative stille and carbonylative stille cross-coupling of tinglycals and sulfonyl chlorides

被引：55

作者：

Dubbaka, SR ^{[1
]}

Steunenberg, P ^{[1
]}

Vogel, P ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, EPFL, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland

来源：

SYNLETT | 2004年 / 07期

关键词：

sulfonyl chlorides; tinglycals; C-glycosides; cross-coupling; catalysis; palladium;

D O I：

10.1055/s-2004-825587

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling of tinglucal and tingalactal derivatives with arenesulfonyl chlorides provides aryl C-glycoside precursors. Desulfitative carbonylative Stille cross-coupling between 1-naphthalenesulfonyl chloride and a tinglucal derivative gives, after stereoselective reduction of the keto moiety and stereoselective oxidative hydroboration, a protected form of 1-[(1S)-2,6-anhydro-L-glycero-D-gulo-heptitol-1-C-yl] naphthalene [beta-C-glucopyranoside of (S)-(naphtha-1-yl)methanol]. Benzyl C-glycoside precursors are obtained by desulfitative Stille coupling of phenylmethanesulfonyl chloride with the corresponding protected tinglycals.

引用

页码：1235 / 1238

页数：4

共 62 条

[41] Novel type of rigid C-linked glycosylacetylene-phenylalanine building blocks for combinatorial synthesis of C-linked glycopeptides [J].

Lowary, T ;

Meldal, M ;

Helmboldt, A ;

Vasella, A ;

Bock, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9657-9668

[42]

MAHLING JA, 1993, SYNTHESIS-STUTTGART, P325

[43] Unified strategy for the synthesis of C-aryl glycosides [J].

Martin, SF .

PURE AND APPLIED CHEMISTRY, 2003, 75 (01) :63-70

[44] Synthesis of α- and β-C-glycosides of N-acetylglucosamine [J].

McGarvey, GJ ;

Schmidtmann, FW ;

Benedum, TE ;

Kizer, DE .

TETRAHEDRON LETTERS, 2003, 44 (19) :3775-3779

[45]

Nicotra F, 1997, TOP CURR CHEM, V187, P55

[46]

Nishikawa T, 1999, SYNLETT, P123

[47] Organotransition metal modified sugars -: Part 12 -: Hydroxynaphthyl C-glycosides via chromium-mediated benzannulation of a sugar alkyne [J].

Paetsch, D ;

Dötz, KH .

TETRAHEDRON LETTERS, 1999, 40 (03) :487-488

[48] Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates [J].

Palmacci, ER ;

Seeberger, PH .

ORGANIC LETTERS, 2001, 3 (10) :1547-1550

[49] Relative reactivities of aminoglycosides and their synthetic equivalents in the C-glycosylation of aromatics.: Synthesis of the pseudoaglycone (D-C-glycoside) of the benzanthrins [J].

Parker, KA ;

Ding, QJ .

TETRAHEDRON, 2000, 56 (52) :10255-10261

[50] Synthesis of some biologically relevant β-C-glycoconjugates [J].

Postema, MHD ;

Piper, JL .

ORGANIC LETTERS, 2003, 5 (10) :1721-1723

← 1 2 3 4 5 6 7 →