Activation of Stable and Recyclable Phenylpropiolate Glycoside (PPG) Donors by Iron Catalysis DOI
Amit Kumar,

Anjali Aghi,

Saksham Mishra

и другие.

Synthesis, Год журнала: 2023, Номер 56(07), С. 1183 - 1199

Опубликована: Окт. 17, 2023

Abstract The glycosylation reaction is one of the important aspects carbohydrate chemistry, where two different units are frequently linked through C–O bonds. In pursuit advancing this field, design and development sustainable catalytic methods for O-glycosylation, which can provide an alternate effective tool to traditional protocols involving stoichiometric promoters classical donors, considered as highly challenging, yet facets glycochemistry. Herein, we report a simple efficient Fe(III)-catalyzed method O-glycosylation activation bifunctional phenylpropiolate glycoside (PPG) donors. This mild involves use inexpensive less toxic FeCl3 catalyst easily synthesizable, benchtop-stable glycosyl ester-based PPG react with various sugar well non-sugar-based acceptors deliver corresponding O-glycosides in good yields moderate anomeric selectivity, along regeneration separable phenylpropiolic acid. Importantly, d-mannose l-rhamnose-based donors afforded high α-anomeric selectivity. conditions were further explored synthesis trisaccharides.

Язык: Английский

Hydrogenation of Sugar Enol-Ethers Using Pd/Et3SiH Reagent System: A Route to Deoxy Sugars/Glycosides DOI

Bindu Tiwari,

Ram Pratap Pandey,

Nazar Hussain

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

We have developed a hydrogenation method using Pd(OAc)2/Et3SiH as reagent system for sugar enol ethers and their glycosides. This approach is highly effective applicable to wide range of glycals glycosides, achieving yields up 96% the corresponding deoxy sugars. Applying standard conditions various O/C-glycosides resulted in excellent transformation 2,3-dideoxy

Язык: Английский

Процитировано

0
Activation of Stable and Recyclable Phenylpropiolate Glycoside (PPG) Donors by Iron Catalysis DOI
Amit Kumar,

Anjali Aghi,

Saksham Mishra

и другие.

Synthesis, Год журнала: 2023, Номер 56(07), С. 1183 - 1199

Опубликована: Окт. 17, 2023

Abstract The glycosylation reaction is one of the important aspects carbohydrate chemistry, where two different units are frequently linked through C–O bonds. In pursuit advancing this field, design and development sustainable catalytic methods for O-glycosylation, which can provide an alternate effective tool to traditional protocols involving stoichiometric promoters classical donors, considered as highly challenging, yet facets glycochemistry. Herein, we report a simple efficient Fe(III)-catalyzed method O-glycosylation activation bifunctional phenylpropiolate glycoside (PPG) donors. This mild involves use inexpensive less toxic FeCl3 catalyst easily synthesizable, benchtop-stable glycosyl ester-based PPG react with various sugar well non-sugar-based acceptors deliver corresponding O-glycosides in good yields moderate anomeric selectivity, along regeneration separable phenylpropiolic acid. Importantly, d-mannose l-rhamnose-based donors afforded high α-anomeric selectivity. conditions were further explored synthesis trisaccharides.

Язык: Английский

Процитировано

0