Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose

Hadžić, Pavle; Vukojević, Nada; Popsavin, Mirjana; Čanadi, Janoš J.

doi:10.2298/jsc0101001h

Cited by 10 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hadzic et al. conducted intensive studies on the reactivities of 3,5‐anhydro furanose sugars towards different anionic nucleophiles, Grignard reagents, and amines and commented that 3,5‐anhydro furanoses bearing an oxetane moiety could behave like non‐carbohydrate molecules under attack by nucleophiles . The 3,5‐anhydro pentafuranose structure was also found in some bioactive small molecules.…”

Section: 5‐anhydro Furanose (26‐dioxabicyclo[320]heptane) and 4mentioning

confidence: 99%

The Construction of Anhydro Monosaccharides

Xie

Lin

et al. 2016

Asian J Org Chem

View full text Add to dashboard Cite

Anhydro monosaccharide is as pecific and distinctive category of carbohydrates, which is found in many naturally deriveda nd artificial bioactive substrates. In the field of organic chemistry,s ome anhydro sugars can be used as common synthons to construct different carbohydrate structures. The development of efficient methodologies for the constructiono fv ariousa nhydro sugar fragments is very important in carbohydrate chemistry,w hich has attracted considerable attention in the past few years. This reviewm ainly covers the development of new synthetic methods since 2000 and gives an overview of the development in the formation of anhydro monosaccharide structures. It systematically summarizes all methodst oe stablish an intramolecular ether bridge in furanose and pyranose structures, which are the mostc ommonly used monosaccharide fragments in carbohydrate chemistry.

show abstract

Section: 5‐anhydro Furanose (26‐dioxabicyclo[320]heptane) and 4mentioning

confidence: 99%

The Construction of Anhydro Monosaccharides

Xie

Lin

et al. 2016

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…Oxetane rings attached directly to a carbohydrate unit rarely occur in literature, due to steric reasons [1]. The most common representatives are 3,5-anhydrofuranose derivatives, which are formed by nucleophilic [2,3] or additive [4] intramolecular ring closure reactions. In addition to the furanoid 3,5-linked oxetanes, there also exists a limited number of 1,2-fused or anomeric spiro-oxetanes having a pyranoid constitution.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses

Bayer

Maichle‐Mößmer

Ziegler

2020

Molbank

View full text Add to dashboard Cite

During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided.

show abstract

“…According to our previous investigations, the opening of the oxetane ring in 3,5-anhydro-1,2-O-cyclohexylidene-a-D-xylofuranose (1) with various nucleophilic reagents (hydrohalogen acids, 9 acetyl haloganides, 11 primary or secondary amines including alkaloids 12 ) always proceeds regioselectively and provides good yields of the corresponding 5-deoxy-5-halo-, 3-O-acetyl-5-deoxy-5-haloand 5-deoxy-5-amino-D-xylofuranose derivatives, respectively. This regioselectivity of nucleophilic oxetane ring opening in 1 is demonstrated this time by hydride reduction of the 3,5-anhydro ring: the reaction proceeds almost quantitatively giving 2 in 97% isolated yield.…”

mentioning

confidence: 99%