124667-93-2Relevant academic research and scientific papers
Synthesis of Antimetabolites of Sucrose
Lay, Luigi,Nicotra, Francesco,Pangrazio, Cristina,Panza, Luigi,Russo, Giovanni
, p. 333 - 338 (2007/10/02)
The C-disaccarides D-glycero-D-ido-D-lyxo-7,11-anhydro-6-deoxydodec-5-ulofuranose-(5,2) 7a and D-glycero-D-ido-D-lyxo-7,11-anhydro-1-O-benzyloxysuccinyl-6-deoxydodec-5-ulofuranose-(5,2) 7b, antimetabolites of sucrose, the second of which is provided with a succinyl group which allows its linkage to biopolymers, have been synthesized.Hydroxymercuriation of the easily available 3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)prop-1-ene 1 followed by iodomercuriation, oxidation, and treatment of the so obtained iodo ketone with triphenylphosphine afforded the stabilized ylide 3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-2-oxopropylidenetriphenylphosphorane 2.Reaction of the ylide 2 with a properly protected D-glyceraldehyde 3 afforded the α,β-unsaturated ketone 4 with a 12-carbon-atom skeleton, the stereoselective osmylation of which, followed by deprotection, gave the C-disaccaride 7a.To obtain the succinylated C-disaccaride 7b, (S)-2-O-benzyl-3-O-(benzyloxysuccinyl)glyceraldehyde 3b was employed, which was obtained by enzymic benzyloxysuccinylation of 2-O-benzylglycerol and subsequent oxidation.
Synthesis of 1-(α-D-Glucopyranosyl)-1-deoxy-D-fructose a Non-metabolisable Analogue of Sucrose
Carkano, Marta,Nicotra, Francesco,Panza, Luigi,Russo, Giovanni
, p. 642 - 643 (2007/10/02)
Reaction of the ylide (6), obtained from the known 1'-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)prop-2-ene (2), with 2,3-O-isopropylidene-D-glyceraldehyde, osmylation of the product (7), and deprotection, affords 1-(α-D-glucopyranosyl)-1-deoxy-D-fructose (1), a C-disaccharide structurally related to sucrose.
