155931-84-3

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 135395-54-9 2(R)-methyl,5(S)-(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine 
• 188744-98-1 C₁₁H₁₅NO₄ 
• 1445800-56-5 (2S,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-3-hydroxy-2-methoxy-2-oxido-1,2-oxaphosphinan-6-yl)methoxy)-2-oxido-1,2-oxaphosphinan-3-yl acetate 
• 1384982-23-3 (2R,3R,5R,6S)-2-((((2S,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-oxido-1,2-oxaphosphinan-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyltribenzoate 
• 1384982-24-4 (2R,3R,4S,5R,6S)-2-((((2R,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-oxido-1,2-oxaphosphinan-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate 

Relevant academic research and scientific papers

Synthesis, characterization, and coupling reactions of six-membered cyclic P-chiral ammonium phosphonite-boranes; Reactive H-phosphinate equivalents for the stereoselective synthesis of glycomimetics

Stereoselective syntheses of P-chiral ammonium phosphonite-borane complexes in the gluco- and manno-like series have been developed from P(V) phostone derivatives. The coupling reactions of these phostone donors with alcohols have been investigated with particular emphasis on the influence of protecting groups and conditions on stereoselectivity. The phosphonite-borane complexes may be applied directly in the coupling reactions and the products oxidized in situ to give phostone-mimetics of disaccharides. On the basis of these studies, successful protocols were established for the synthesis of β-gluco and α- and β-manno-configured phostones of primary alcohols. Deprotection of the dimeric compounds leads to novel families of α- or β-(1→6)-linked glycomimetics.

Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy

Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D- arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino- hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D

Cyclic Phosphonate Analogs of Hexopyranoses

Acyclic and cyclic analogs of D-glucopyranose and D-mannopyranose have been prepared in which the anomeric carbon has been replaced with a phosphorus.Base-catalyzed addition of dimethyl phosphite to di-O-isopropylidene-D-arabinose followed by recrystallization yields only the acyclic gluco-isomer, through what appears to be a selective recrystallization process.The use of diethyl phosphite under similar conditions yielded only the acyclic manno-isomer.The stereochemistry of each was ascertained through comparison of the pentaacetylated derivatives 11 and 12.For the cyclic analogs 1 and 2, synthesis consists of acid-catalyzed trimethyl phosphite addition to the carbonyl of a hydroxyl-protected open-chain D-arabinose derivative, removal of a formate ester from the 4-hydroxyl group, and base-catalyzed transesterification/cyclization.All four possible cyclic α-hydroxy phosphonate diastereomers were synthesized in roughly equal amounts.Complete separation of the gluco- and manno-isomers was accomplished, and Homonuclear two-dimensional J-spectroscopy was used to supplement standard NMR analysis in order to completely characterize the isolated diastereomers 21 and 22 and assign gluco- and manno-stereochemistry, respectively.