201290-06-4

Upstream product

• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 16838-89-4 2,3,5-tri-O-benzyl-D-lyxofuranoside 
• 100-39-0 benzyl bromide 
• 1824-96-0 methyl xylofuranoside 
• 87-72-9 D-Xylose 

Downstream Products

• 302800-96-0 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-xylo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate 
• 904893-23-8 (3S,4R,5R)-5-methanesulfonyloxy-3,4,6-tribenzyloxy-1-hexene 
• 1338246-46-0 C₃₃H₄₄O₄Si 
• 1337989-81-7 tert-butyldimethyl((2R,3R,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane 
• 1337989-82-8 5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde 
• 1337989-83-9 5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3R,4R,5R)-3,46-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-oxohexyl)-1H-pyrrole-2-carbaldehyde 
• 1337989-84-0 (2S,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 
• 1337990-05-2 (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 
• 1392126-48-5 (+)-(2R,3R,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yl 4-nitrobenzenesulfonate 
• 1392126-53-2 (-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate 
• 1392126-56-5 (-)-(2R,3R,4R,5R)-1,3,4-tris(benzyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate 
• 1392126-83-8 (-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 
• 1392126-73-6 (-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate 
• 171721-09-8 (-)-4-amino-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one 

Relevant academic research and scientific papers

A stereoselective approach to β-L-arabino nucleoside analogues: Synthesis and cyclization of acyclic 1′,2′-syn N, O-Acetals

Reported herein is a novel and versatile strategy for the stereoselective synthesis of unnatural β-l-arabinofuranosyl nucleoside analogues from acyclic N,OTMS-acetals bearing pyrimidine and purine bases. These unusual acetals undergo a C1′ to C4′ cyclization where the OTMS of the acetal serves as the nucleophile to generate 2′-oxynucleosides with complete retention of configuration at the C1′ acetal center. N,OTMS-acetals are obtained diastereoselectively from additions of silylated nucleobases onto acyclic polyalkoxyaldehydes in the presence of MgBr 2·OEt2. The strategy reported is addressing important synthetic challenges by providing stereoselective access to unnatural l-nucleosides starting from easily accessible pools of d-sugars and, as importantly, by allowing the formation of the sterically challenging 1′,2′-cis nucleosides. A wide variety of nucleoside analogues were synthesized in 7-8 steps from easily accessible d-xylose.

An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis

A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.