178491-57-1

Upstream product

• 100-39-0 benzyl bromide 

Downstream Products

• 178491-58-2 ethyl 1,4,6-tri-O-benzyl-2-thio-α-D-fructofuranoside 
• 178491-60-6 ethyl 1,4,6-tri-O-benzyl-2-thio-β-D-fructofuranoside 
• 178491-59-3 ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-α-D-fructofuranoside 
• 203056-97-7 ethyl 1,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-2-thio-β-D-fructofuranoside 
• 203056-91-1 α-ethoxy α-(ethyl 1,4,6-tri-O-benzyl-2-thio-α-D-fructofuranosid-3-O-yl)-4-methoxytoluene 
• 1053696-63-1 (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 

Relevant academic research and scientific papers

A novel β-directing fructofuranosyl donor concept. Stereospecific synthesis of sucrose

A new concept for the construction of β-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the α-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give β-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

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.