367922-37-0

Upstream product

• 67-56-1 methanol 
• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate 

Downstream Products

• 402948-43-0 methyl (phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-42-5 methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-(tert-butoxycarbonylamino)-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-41-4 methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-(allyloxycarbonylamino)-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-44-7 methyl (phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-45-8 methyl (phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trichloroacetamido-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-40-3 methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-(benzyloxycarbonylamino)-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 688013-43-6 methyl (phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-(9-fluorenylmethoxycarbonylamino)-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 944560-92-3 5-azidoacetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-thiophenyl-1-methyl ester 

Relevant academic research and scientific papers

The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect

The synthesis of α-sialosides is one of the most difficult reactions in carbohydrate chemistry and is considered to be both a thermodynamically and kinetically disfavored process. The use of acetonitrile as a solvent is an effective solution for the α-sel

An efficient approach to the discovery of potent inhibitors against glycosyltransferases

We describe a standardized approach for searching potent and selective inhibitors of glycosyltransferases by high throughput quantitative MALDI-TOFMS-based screening of focused compound libraries constructed by 1,3-dipolar cycloaddition of the desired azidosugar nucleotides with various alkynes. An aminooxy-functionalized reagent with a stable isotope was conjugated with oligosaccharides to afford glycopeptides as acceptor substrates with improved ion sensitivity. Enhanced ionization potency of new substrates allowed for MALDI-TOFMS-based facile and quantitative analysis of enzymatic glycosylation in the presence of glycosyl donor substrates. A non-natural synthetic sugar nucleotide was identified to be the first highly specific inhibitor for rat recombinant α2,3-(N)-sialyltransferase (α2,3ST, IC50 = 8.2 μM), while this compound was proved to become a favorable substrate for rat recombinant α2,6-(N)-sialyltransferase (α2,6ST, Km = 125 μM). Versatility of this strategy was demonstrated by identification of two selective inhibitors for human recombinant α1,3-fucosyltransferase V (α1,3-FucT, Ki = 293 nM) and α1,6-fucosyltransferase VIII (α1,6-FucT, Ki = 13.8 μM).

Stereoselective synthesis of α(2,9) di- to tetrasialic acids, using a 5,4-N,O-carbonyl protected thiosialoside

(Chemical Equation Presented) An efficient stereoselective synthesis of α(2,9) tetra- to disialic acids 1-3, using the 5,4-N,O-carbonyl protected thiosialoside 4, is described. The cyclic protecting group was effective for α-sialylation without the need f

Synthetic study on α(2→8)-linked oligosialic acid employing 1,5-lactamization as a key step

An attempt to synthesize α(2→8)-linked oligosialic acid utilizing a 1,5-lactamized sialyl acceptor is described. 1,5-Lactamization was experimentally proven to proceed only for α-sialoside, which was integrated into the synthetic cycle of oligosialic acid

Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivity

A 5-N,7-O-oxazinanone derivative of a thiosialic acid ester has been synthesized and investigated for the effect of conformational restriction on glycosylation. The cyclic group is found to be powerfully disarming, but to have no beneficial effect on reac

Stereoselective synthesis of oligo-α-(2,8)-sialic acids

An efficient and elegant synthesis of α(2,8)-oligosialosides is described. The 5-N,4-O-carbonyl-protected sialyl donor undergoes α-sialylation in CH2Cl2 to give α(2,8)- and α(2,9)-disialosides in excellent yields. The 5-N,4-O-carbony

One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-β-thiophenyl sialoside

We describe an efficient synthesis of 2,6- and 2,3-sialyl T antigens linked to serine in a one-pot glycosylation. We first investigated the glycosidation of thiosialosides by varying the N-protecting group. Modification of the C-5 amino group of β-thiosialosides into the N-9-fluorenylmethoxycarbonyl, N-2,2,2-trichloroethoxycarbonyl (N-Troc), and N-trichloroacetyl derivatives enhanced the reactivity of these compounds towards glycosidation. Addition of a minimum amount of 3 A molecular sieves was also effective in improving the yield of α-linked sialosides. Next, we conducted one-pot syntheses of the glycosyl amino acids by using the N-Troc sialyl donor. The N-Troc derivative can be converted into the N-acetyl derivative without racemization of the amino acids. Branched-type one-pot glycosylation, initiated by regioselective glycosylation of the 3,6-dihydroxy galactoside with the N-Troc-β-thiophenyl sialoside, provided the protected 2,6-sialyl T antigen in good yield. Linear-type one-pot glycosylation, initiated by chemoselective glycosylation of galactosyl fluoride with the N-Troc-β-thiophenyl sialoside, afforded the protected 2,3-sialyl T antigen in excellent yield. Both protected glycosyl amino acids were converted into the fully deprotected 2,6- and 2,3-sialyl T antigens linked to serine in good yields.

An effective sialylation method using N-Troc- and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen

We describe an efficient sialylation method using β-thiosialosides with various N-protecting groups. Modification of the C-5 amino group of β-thiosialosides into N-Fmoc and N-Troc derivatives enhanced their reactivity in glycosidation. In addition, a minimum amount of MS-3 A? was effective to improve the yield of α-linked sialoside. Branched type one-pot glycosylation initiating glycosidation of the N-Troc-protected β-thiophenyl sialoside at a primary alcohol provided the protected 2,6-sialyl-T antigen in good yield, which was converted to the fully deprotected glycosyl amino acid.

Synthesis of a sialic acid dimer derivative, 2′α-O-benzyl Neu5Ac-α-(2→5)Neu5Gc

The preparation of a disaccharide 2, Neu5Ac-α-(2→5)Neu5Gc having a α-benzyl protecting group at the reducing end, by the coupling of the easily accessible building units 4 and 5 is described. Subsequent deprotection of the coupling adduct led to the isolation of the target compound 2 in high yield.