1053696-63-1

Basic information

• Product Name: (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-[((2R,3S,4R,5R)-4-benzyloxy-2,5-bis-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-furan-3-yloxy)-(4-methoxy-phenyl)-methoxymethyl]-6-methoxy-tetrahydro-pyran
• CAS NO: 1053696-63-1
• Molecular Weight: 1077.35
• Mol File: 1053696-63-1.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-[((2R,3S,4R,5R)-4-benzyloxy-2,5-bis-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-furan-3-yloxy)-(4-methoxy-phenyl)-methoxymethyl]-6-methoxy-tetrahydro-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-[((2R,3S,4R,5R)-4-benzyloxy-2,5-bis-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-furan-3-yloxy)-(4-methoxy-phenyl)-methoxymethyl]-6-methoxy-tetrahydro-pyran(1053696-63-1)
• EPA Substance Registry System: (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-[((2R,3S,4R,5R)-4-benzyloxy-2,5-bis-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-furan-3-yloxy)-(4-methoxy-phenyl)-methoxymethyl]-6-methoxy-tetrahydro-pyran(1053696-63-1)

Safety Data

• Hazardous Substances Data: 1053696-63-1(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 178491-58-2 ethyl 1,4,6-tri-O-benzyl-2-thio-α-D-fructofuranoside 
• 178491-57-1 1,4,6-tri-O-benzyl-2,3-O-[1-(benzyloxy)benzylidene]-β-D-fructofuranose 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 178491-59-3 ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-α-D-fructofuranoside 

Relevant articles and documents

Stereospecific Synthesis of β-D-Fructofuranosides Using Thioglycoside Donors and Internal Aglycon Delivery

Stereospecific synthesis of β-D-fructofuranosides has been accomplished by the application of an internal acceptor delivery approach. The acceptor, ethanol or monosaccharides, is initially tethered to the fructofuranose 3-hydroxyl group, adjacent to the anomeric center and on the β-side of the furanose ring, as part of a mixed p-methoxybenzaldehyde acetal, which is formed by DDQ-oxidation of ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-D-fructofuranoside in the presence of the acceptor or of the p-methoxybenzylated acceptor in the presence of the corresponding 3-OH fructofuranoside. Then, activation of the thioglycoside with a thiophilic promoter allows the delivery of the acceptor from the acetal to the activated anomeric center to yield the β-linked fructofuranoside in high yields (76-85%). If promoters with nonnucleophilic anions (triflate, perchlorate) are used, the intermediate acetal decomposes to produce the β-fructofuranoside products as 3-OH derivatives. However, if NIS is used as promoter, the N-succinimide anion interacts with the benzylidene carbon to give the β-fructofuranoside products as mixed fructofuranoside-3-O-yl N-succinimide p-methoxybenzaldehyde acetals.