Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals

Chéry, Florence; Cabianca, Elena; Tatibouët, Arnaud; Lucchi, Ottorino De; Rollin, Patrick

doi:10.1016/j.carres.2015.09.011

Cited by 6 publications

(3 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…147–152 4-Methoxybenzylidene acetals can also be selectively opened in a similar fashion and using similar reagents to as benzylidene acetals. 153,154 Regioselective opening of other acetals including 4,6- O -prop-2-enylidene, 132 fluorous benzylidene 155 phenylsulfonylethylidene 156 has also been explored. Oxidative and photooxidative methods for opening of benzylidene acetal have also been developed.…”

Section: Synthesis Of Partially Substituted Building Blocks By Regiosmentioning

confidence: 99%

Synthesis of carbohydrate building blocksviaregioselective uniform protection/deprotection strategies

Wang

Demchenko

2019

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of Partially Substituted Building Blocks By Regiosmentioning

confidence: 99%

Synthesis of carbohydrate building blocksviaregioselective uniform protection/deprotection strategies

Wang

Demchenko

2019

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…The only known examples of single electron transfer (SET) mediated transformations involve the opening of 2‐phenylsulfonylethylidene (PSE) acetals . PSE acetals were introduced by Chéry et al in 2000, and have proven to be useful protecting groups in carbohydrate chemistry , .…”

Section: Furansmentioning

confidence: 99%

“…The SET mediated fragmentation of PSE acetals on pyranoses has been explored by Chéry and co‐workers . Following earlier studies on simple PSE acetals, the researchers employed either sodium amalgam (Na/Hg), magnesium in methanol or samarium(II) iodide (SmI 2 ) for methylglucoside 179 to accomplish fragmentation (Table ).…”

Section: Pyransmentioning

confidence: 99%

Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

et al. 2018

View full text Add to dashboard Cite

The (regio)selective manipulation of hydroxyl groups in carbohydrates has been a long‐standing challenge in (bio)organic chemistry and continues to trigger the creative minds of many chemists. Among the various strategies that have been developed to address these issues, mostly relying on multistep procedures involving the use of protecting groups, the regioselective ring opening of 1,3‐dioxane‐type acetals has emerged as a powerful tool. Since the first papers on this subject appeared in the 1960s, a large variety in both acetal types and reagents for their partial cleavage has come to the fore. This review aims to give an overview of the different carbohydrate‐derived ring systems, ranging from four‐ to seven‐membered rings, on which regioselective ring‐openings have been performed, along with the appropriate reagents and combinations thereof. The transformations on 1,3‐dioxane acetals fit in a larger group of ring opening reactions of structurally related cyclic functional groups, including 1,3‐dioxolanes, 1,3‐oxathianes, orthoesters, cyclic carbonates and silylene acetals, which will not be discussed in this review.

show abstract

Strategies Toward Protection of 1,2‐ and 1,3‐Diols in Carbohydrate Chemistry

Schuler¹,

Tatibouët²

2018

Protecting Groups

View full text Add to dashboard Cite

Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals

Cited by 6 publications

References 17 publications

Synthesis of carbohydrate building blocksviaregioselective uniform protection/deprotection strategies

Synthesis of carbohydrate building blocksviaregioselective uniform protection/deprotection strategies

Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

Strategies Toward Protection of 1,2‐ and 1,3‐Diols in Carbohydrate Chemistry

Contact Info

Product

Resources

About