339276-14-1Relevant articles and documents
Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors
Li, Xiaona,Li, Chenyu,Liu, Rongkun,Wang, Jiazhe,Wang, Zixuan,Chen, Yan,Yang, You
, p. 9693 - 9698 (2019)
A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wid
2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides
Liu, Xianglai,Lin, Yetong,Liu, Ao,Sun, Qianhui,Sun, Huiyong,Xu, Peng,Li, Guolong,Song, Yingying,Xie, Weijia,Sun, Haopeng,Yu, Biao,Li, Wei
, p. 443 - 452 (2021/12/27)
The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car
OFox imidates as versatile glycosyl donors for chemical glycosylation
Nigudkar, Swati S.,Wang, Tinghua,Pistorio, Salvatore G.,Yasomanee, Jagodige P.,Stine, Keith J.,Demchenko, Alexei V.
, p. 348 - 359 (2017/01/13)
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
3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry
Andersen, Sofie Meng,Heuckendorff, Mads,Jensen, Henrik H.
supporting information, p. 944 - 947 (2015/04/14)
Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors
Yu, Biao,Tao, Houchao
, p. 2405 - 2407 (2007/10/03)
Glycosyl (N-phenyl)trifluoroacetimidates, readily prepared from 1-hydroxyl sugars by treatment with (N-phenyl)trifluoroacetimidoyl chloride in the presence of K2CO3, were demonstrated to be effective glycosyl donors.