73045-57-5Relevant academic research and scientific papers
A tin-free regioselective radical de-o-benzylation by an intramolecular hydrogen atom transfer on carbohydrate templates
Attouche, Angie,Urban, Dominique,Beau, Jean-Marie
, p. 9572 - 9575 (2013/09/23)
Radically selective: A remarkable 1,7-hydrogen atom transfer of a benzylic hydrogen atom to an O-silylmethylene radical initiates a regioselective de-O-benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups. Copyright
Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides
Nagatsuka, Takayuki,Yamaguchi, Shuhei,Totani, Kiichiro,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 519 - 535 (2007/10/03)
The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.
Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates
Nagatsuka,Yamaguchi,Totani,Takao,Tadano
, p. 481 - 484 (2007/10/03)
The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.
Acceptor-Substrate Recognition by N-Acetylglucosaminyltransferase-V: Role of the Mannose Residue in βDGlcNAc(1->2)αDMan(1->6)βDGlcOR
Khan, Shaheer H.,Duus, Jens Oe.,Crawley, Suzanne C.,Palcic, Monica M.,Hindsgaul, Ole
, p. 2415 - 2436 (2007/10/02)
βGlcNAc(1->2)αMan(1->6)βGlc-O(CH2)7CH3 (4) is an acceptor specific for N-acetylglucosaminyltransferase-V (GlcNAcT-V), a branching enzyme controlling the biosynthesis of cell-surface Asn-linked oligosaccharides.Three analogs of 4, where the central mannose
Synthesis of Standardized Building Blocks as a β-D-Mannosyl Donors with a Temporary Protection to be 3,6-Di-O-glycosyl Acceptors, for Constructing the Inner Core of Glycoproteins and Artificial Antigens
El Ashry, El Sayed H.,Schuerch, Conrad
, p. 1581 - 1586 (2007/10/02)
A synthetic scheme has been achieved for the core block of glycoproteins having D-mannose configuration, which is standardized to be a 3,6-di-O-glycosyl acceptor and react stereoselectively as a β-D-mannosyl donor.The synthesis was started by methyl 2,3-O
