374900-65-9

Upstream product

• 108-24-7 acetic anhydride 
• 157903-84-9 3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene 
• 75-05-8 acetonitrile 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 406487-96-5 2-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethyl aldehyde 
• 1182839-35-5 (2R)-1-[methyl 2,3,4-tri-O-benzyl-α-D-xylopyranosidyl]-6-[2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-α-D-1-C-glucopyranosyl]-4-hexen-2-ol 
• 374900-72-8 1-C-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)propane 
• 374900-73-9 1-C-(2,3,6-tri-O-benzyl-α-D-xylo-hex-4-ulopyranosyl)propane 
• 374900-71-7 1-C-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)propane 
• 374900-66-0 3-C-(3,6-di-O-benzyl-4-deoxy-α-D-glycero-2-ulopyranosyl)propene 
• 374900-70-6 1-C-(4,6-O-benzylidene-α-D-glucopyranosyl)propane 
• 184155-60-0 3-C-(3,4,6-tri-O-benzyl-α-D-arabino-hex-2-ulopyranosyl)propene 
• 618387-40-9 2-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-mannopyranosyl)ethyl aldehyde 
• 192929-44-5 Trifluoro-methanesulfonic acid (2R,3S,4S,5R,6R)-2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 184290-85-5 3-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-mannopyranosyl)-propene 

Relevant academic research and scientific papers

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

An approach to the synthesis of pseudo-oligosaccharides based on the cross-metathesis reaction between distinct sugar-olefins, followed by intramolecular cyclization of the obtained heterodimer, is presented. In particular, the relative efficiency of two

Stereoselective synthesis of dioxabicycles from 1-C-allyl-2-O-benzyl- glycosides - An intramolecular cyclization between 2-O-benzyl oxygen and the allyl double bond

Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium in

Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: A stereospecific rearrangement initiated by base

Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4α, 4β, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a β elimination to afford α,β-unsaturated C-ulopyranosyl compounds (5α, 5β, and 12), which further rearranged in a stereocontrolled manner to multifunctionalized α,β-cyclopentenones (6 and 14) in 70-80% yield. Both C-α- and C-β-2-ulosides (5α and 5β) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5α yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5α during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used.