370554-13-5

Upstream product

• 930-69-8 sodium thiophenolate 
• 370554-12-4 (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 108-98-5 thiophenol 
• 625388-51-4 (2S,4aR,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 100-39-0 benzyl bromide 
• 819798-40-8 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 197663-19-7 phenyl-2-azido-2-deoxy-1-thio-D-galactopyranoside 

Downstream Products

• 370554-14-6 O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester 
• 1356031-18-9 phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 1372074-05-9 phenyl 4-O-(2-azido-3-O-benzoyl-4-phthalimido-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 1356031-22-5 phenyl 4-O-(2-azido-4-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 1454689-90-7 cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 1454689-91-8 cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside 
• 1454689-89-4 cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonyl]amino-β-D-galactopyranoside 
• 1454689-86-1 phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside 
• 1454689-85-0 phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-[(2,2,2-trichloroethoxy)carbonyl]amino-β-D-galactopyranoside 
• 370554-15-7 O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester 

Relevant academic research and scientific papers

Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: Verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds

The effect of a 4,6-O-alkylidene acetal on the rate of acid-catalyzed hydrolysis of methyl galactopyranosides and of spontaneous hydrolysis of 2,4-dinitrophenyl galactopyranosides has been studied through the synthesis and hydrolysis of analogs in which O6 is replaced by a methoxymethylene unit in which the methoxy group adopts either an equatorial or an axial position according to the configuration. Consistent with earlier studies under both acid-catalyzed and spontaneous hydrolysis conditions, the alkylidene acetal, or its 7-carba analog, retards hydrolysis with respect to comparable systems lacking the cyclic protecting group. The configuration at C6 in the 7-carba analogs does not influence the rate of acid-catalyzed hydrolysis but has a minor influence on the rate of spontaneous hydrolysis of the 2,4-dinitrophenyl galactosides, confirming earlier studies on the role played by the hydroxymethyl group conformation on glycoside reactivity. The benzylidene acetal is found to stabilize the α-anomer of galactopyranose derivatives relative to monocyclic analogs. Reasons for the α-selectivity of 4,6-O-benzylidene- protected galactopyranosyl donors bearing neighboring group-active protecting groups at O2 are discussed.

Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae

The lipoteichoic acid repeating unit of Streptococcus pneumoniae is a complex pseudopentasaccharide (3). It consists of one ribitol-phosphate, one 2-acetamino-4-amino-2,4,6-trideoxy-galactose, one glucose and two galactosamine residues each differently li

METHOD OF SYNTHESIZING SUGAR CHAIN

An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a metho

Convergent total syntheses of oligosaccharides by one-pot sequential stereoselective glycosylations

A convergent total synthesis of F1α antigen, a member of the tumor-associated O-linked mucin glycosyl amino acid, was tried by one-pot sequential glycosylation. Highly α-selective glycosylation of amino acid 7 with thioglycoside 6 was successfully carried out by combining trityl trifluoromethanesulfonate (TrOTf) and N-iodosuccimide (NIS) which gave glycosyl amino acid 21 in high yield (97%, α/β = 83/17). Next, the glycosylation of thioglycoside 4 with galactosyl phenyl carbonate 2 or fluoride 3 was tried by the promotion of trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] or trifluoromethanesulfonic acid (TfOH); protected F1α 25 was afforded in 80 or 89% overall yield, respectively, by the further addition of glycosyl amino acid 5 and NIS. The desired trisaccharide was obtained in high yield after removal of the protecting groups. Next, a convergent total synthesis of branched hepta-β-glucoside 30 having phytoalexin-elicitor activity was efficiently performed by way of two one-pot sequential glycosylation reactions: that is, trisaccharide 34 was synthesized in high yield by TfOH-catalyzed one-pot glycosylation using three given monosaccharides (31, 35, and 36) as shown in Scheme 12 and by subsequent selective deprotection of 6′-O-TBDPS group. The second one-pot glycosylation of trisaccharide 34 with three monosaccharides (31, 32, and 33d) also proceeded smoothly to afford heptaglucoside 43 stereoselectively in 48% total yield based on monosaccharide 32. Phytoalexin-elicitor active branched hepta-β-glucoside 30 was afforded by the sequential deprotection.

A convergent total synthesis of the mucin related F1α antigen by one-pot sequential stereoselective glycosylation

A convergent total synthesis of F1α antigen, a member of the tumor-associated O-linked mucin glycosyl amino acids, was accomplished by one-pot sequential glycosylation. In the first step, the corresponding disaccharide was formed from galactosyl phenylcarbonate 2 or fluoride 3 and thioglycoside 4 by the promotion of TrB(C6F5)4 or TfOH, and following glycosylation of glycosyl amino acid 5 by further addition of N-iodosuccinimide(NIS) afforded protected F1α in 80 or 89% overall yield, respectively. By the subsequent deprotection, F1α antigen was obtained in good yield.