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

[41] C-glycosyl tyrosines.: Synthesis and incorporation into C-glycopeptides
Pearce, AJ
Ramaya, S
Thorn, SN
Bloomberg, GB
Walter, DS
Gallagher, T
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15): : 5453 - 5462
[42] Synthesis of C-glycosyl β-amino acids by asymmetric Mannich-type three-component reactions
Dondoni, A
Massi, A
Sabbatini, S
Bertolasi, V
TETRAHEDRON LETTERS, 2004, 45 (11) : 2381 - 2384
[43] Synthesis of thiourea-tethered C-glycosyl amino acids via isothiocyanate-amine coupling
Barghash, Reham F.
Massi, Alessandro
Dondoni, Alessandro
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (16) : 3319 - 3330
[44] Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction
Sipos, Szabolcs
Jablonkai, Istvan
Egyed, Orsolya
Czugler, Matyas
CARBOHYDRATE RESEARCH, 2011, 346 (18) : 2862 - 2871
[45] SYNTHETIC C-GLYCOSYL NUCLEOSIDES - A NEW APPROACH
CHAPLEUR, Y
CASTRO, B
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12): : 2683 - 2685
[46] The overlooked rotational isomerism of C-glycosyl flavonoids
Guohong Zhou
Renliang Yan
Xiaogen Wang
Shaolin Li
Jin Lin
Jia Liu
Zhendong Zhao
Phytochemistry Reviews, 2019, 18 : 443 - 461
[47] C-glycosyl flavones from Peperomia blanda
Velozo, Leosvaldo S. M.
Ferreira, Marcelo J. P.
Santos, Maria Isabel S.
Moreira, Davyson L.
Guimaraes, Elsie F.
Emerenciano, Vicente P.
Kaplan, Maria Auxiliadora C.
FITOTERAPIA, 2009, 80 (02) : 119 - 122
[48] THE STRUCTURE ELUCIDATION OF A NOVEL C-GLYCOSYL SIDEROPHORE
FU, JM
BELL, CL
VENTON, DL
WAWSZKIEWICZ, EJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 188 (AUG): : 107 - MEDI
[49] The overlooked rotational isomerism of C-glycosyl flavonoids
Zhou, Guohong
Yan, Renliang
Wang, Xiaogen
Li, Shaolin
Lin, Jin
Liu, Jia
Zhao, Zhendong
PHYTOCHEMISTRY REVIEWS, 2019, 18 (02) : 443 - 461
[50] A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids
Paterson, DE
Griffin, FK
Alcaraz, ML
Taylor, RJK
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (07) : 1323 - 1336

← 1 2 3 4 5 →