De Novo Synthesis of Mono- and Oligosaccharides via Dihydropyran Intermediates.
The importance of carbohydrates is evident by their essential role in all living systems. Their syntheses have attracted attention from chemists for over a century. Most chemical syntheses in this area focus on the preparation of carbohydrates from naturally occurring monosaccharides. De novo chemical synthesis of carbohydrates from feedstock starting materials has emerged as a complementary method for the preparation of diverse mono- and oligosaccharides. In this review, the history of de novo carbohydrate synthesis is briefly discussed and particular attention is given to methods that address the formation of glycosidic bonds for potential de novo synthesis of oligosaccharides. Almost all methods of this kind involve the formation of dihydropyran intermediates. Recent progress in forming dihydropyrans by Achmatowicz rearrangement, hetero-Diels-Alder cycloaddition, ring-closing metathesis, and other methods is also elaborated.
School of Pharmacy, University of Wisconsin-Madison, Madison, WI, 53705, USA.|School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, P.R. China.
Wangze
W
Song
School of Pharmacy, Hainan Medical University, Haikou, 571199, P.R. China.
Shuojin
S
Wang
School of Pharmacy, University of Wisconsin-Madison, Madison, WI, 53705, USA.|Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.
Weiping
http://orcid.org/0000-0002-0039-3196
W
Tang
D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*
D009005:Monosaccharides; D009844:Oligosaccharides; D011714:Pyrans
carbohydrates; de novo synthesis; natural products; oligosaccharides; synthesis design