OFox imidates as versatile glycosyl donors for chemical glycosylation

被引：16

作者：

Nigudkar, Swati S. ^{[1
]}

Wang, Tinghua ^{[1
]}

Pistorio, Salvatore G. ^{[1
]}

Yasomanee, Jagodige P. ^{[1
]}

Stine, Keith J. ^{[1
]}

Demchenko, Alexei V. ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem & Biochem, One Univ Blvd, St Louis, MO 63121 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 02期

关键词：

BUILDING-BLOCKS; DEHYDRATIVE GLYCOSYLATION; OLIGOSACCHARIDE SYNTHESIS; 1,2-CIS GLYCOSYLATION; EFFICIENT ACTIVATION; THIOGLYCOSIDES; MECHANISM; GLYCOSIDATION; ANHYDRIDE; CHEMISTRY;

D O I：

10.1039/c6ob02230h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previously we communicated 3,3-difluoroxindole (HOFox) - mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical 1,2-cis and 1,2-trans glycosylation.

引用

页码：348 / 359

页数：12

共 50 条

[41] Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation
Wang, Tinghua
Singh, Yashapal
Stine, Keith J.
Demchenko, Alexei V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (47) : 6699 - 6705
[42] Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation
Ranade, Sneha C.
Kaeothip, Sophon
Demchenko, Alexei V.
ORGANIC LETTERS, 2010, 12 (24) : 5628 - 5631
[43] Common side reactions of the glycosyl donor in chemical glycosylation
Christensen, Helle M.
Oscarson, Stefan
Jensen, Henrik H.
CARBOHYDRATE RESEARCH, 2015, 408 : 51 - 95
[44] PHENYLSELENOGLYCOSIDES AS NOVEL, VERSATILE GLYCOSYL DONORS - SELECTIVE ACTIVATION OVER THIOGLYCOSIDES
MEHTA, S
PINTO, BM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 35 - CARB
[45] PHENYLSELENOGLYCOSIDES AS NOVEL, VERSATILE GLYCOSYL DONORS - SELECTIVE ACTIVATION OVER THIOGLYCOSIDES
MEHTA, S
PINTO, BM
TETRAHEDRON LETTERS, 1991, 32 (35) : 4435 - 4438
[46] 6-O-glycosylation of morphine derivatives using thioglycosides as glycosyl donors
Rukhman, I
Yudovich, L
Nisnevich, G
Gutman, AL
SYNTHESIS-STUTTGART, 2000, (09): : 1241 - 1246
[47] Synthesis of lupane saponins from acetylated glycosyl donors by acetonitrile directed glycosylation
Kuczynska, Kinga
Pakulski, Zbigniew
TETRAHEDRON, 2015, 71 (19) : 2900 - 2905
[48] Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
Tian, Qiang
Zhang, Shuo
Yu, Qian
He, Mei-Bo
Yang, Jin-Song
TETRAHEDRON, 2007, 63 (10) : 2142 - 2147
[49] Gold-Catalyzed Activation of Glycosyl Donors with Alkyne Moieties for Glycosylation Reaction
Inuki, Shinsuke
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (01) : 69 - 70
[50] Stereoselective Organocatalyzed Glycosylation of Glycosyl Trichloroacetimidate Donors: Thiouracil as Bronsted Acid Catalyst
Tiwari, Ashwani
Khanam, Ariza
Lal, Mohan
Mandal, Pintu Kumar
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (15) : 3262 - 3268

← 1 2 3 4 5 →