Synthesis of C-glycosyl lactones and protected C-glycosyl amino acids:: Use of radical cyclization

被引：23

作者：

Zhang, JH ^{[1
]}

Clive, DLJ ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 03期

关键词：

D O I：

10.1021/jo981435w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protected carbohydrates 6a-13a, having one free hydroxyl and a phenylseleno group or halogen on the adjacent carbon, were condensed with (2,2-diphenylhydrazono)acetic acid (2); the resulting esters undergo radical cyclization to afford carbohydrates fused to a 2,2-diphenylhydrazino lactone unit (6c,d-13c,d). In suitable cases (9c,d) such carbohydrate lactones can be elaborated into C-glycosyl amino acids.

引用

页码：770 / 779

页数：10

共 50 条

[31] The preparation of C-glycosyl amino acids -: an examination of olefin cross-metathesis
Schmidtmann, FW
Benedum, TE
McGarvey, GJ
TETRAHEDRON LETTERS, 2005, 46 (27) : 4677 - 4681
[32] C-GLYCOSYL PRECURSORS FOR TRICHOTHECANE SYNTHESES
FRASERREID, B
TSANG, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 187 (APR): : 87 - ORGN
[33] C-GLYCOSYL DERIVATIVES .37.
TRONCHET, JMJ
GENTILE, B
HELVETICA CHIMICA ACTA, 1979, 62 (04) : 977 - 984
[34] SYNTHESIS OF C-GLYCOSYL SUBSTITUTED OF BETA-CARBOLINE
ZHDANOV, YA
KORNILOV, VI
DOROFEEN.GN
DOKLADY AKADEMII NAUK SSSR, 1968, 178 (04): : 849 - &
[35] Total synthesis of α-C-mannosyltryptophan, a naturally occurring C-glycosyl amino acid
Nishikawa, T
Ishikawa, M
Wada, K
Isobe, M
SYNLETT, 2001, : 945 - 947
[36] A novel general route for the synthesis of C-glycosyl tyrosine
Brenna, E
Fuganti, C
Grasselli, P
Serra, S
Zambotti, S
CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (08) : 1872 - 1878
[37] Synthesis of new C-glycosyl aza-β3-amino acids building blocks
Andreini, Manuel
Felten, Anne-Sophie
Thien, Hoang-Trang Tran
Taillefumier, Claude
Pellegrini-Moise, Nadia
Chapleur, Yves
TETRAHEDRON LETTERS, 2012, 53 (22) : 2702 - 2705
[38] C-Glycosyl compounds in the synthesis of analogs of the phytotoxin diplopyrone
Giuliano, Robert
Rosano, Rob
Lazzara, Nicholas
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[39] THE SYNTHESIS OF 2-AZIDO C-GLYCOSYL SUGARS
BERTOZZI, CR
BEDNARSKI, MD
TETRAHEDRON LETTERS, 1992, 33 (22) : 3109 - 3112
[40] FURAN-BASED SYNTHESIS OF C-GLYCOSYL CARBOXYLATES
DONDONI, A
MARRA, A
SCHERRMANN, MC
TETRAHEDRON LETTERS, 1993, 34 (45) : 7323 - 7326

← 1 2 3 4 5 →