220774-86-7

Upstream product

• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 76-83-5 trityl chloride 

Downstream Products

• 220774-88-9 (2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol 
• 741677-79-2 phenyl 3,4-O-isopropylidene-1-thio-6-O-triphenylmethyl-β-D-galactopyranoside 
• 864776-74-9 C₂₉H₂₄ClFO₉ 
• 864776-73-8 phenyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranoside 
• 864776-75-0 C₆₃H₅₄ClNO₁₅S 
• 139608-11-0 phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside 
• 187031-78-3 methyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 187031-76-1 tert-butyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 187031-86-3 benzyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 225640-42-6 benzyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 
• 225640-49-3 methyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 1190749-37-1 phenyl 3-O-(2-naphthylmethyl)-6-O-trityl-1-thio-β-D-galactopyranoside 
• 741677-98-5 phenyl 2,3,4-tri-O-(4-methoxyphenylmethyl)-1-thio-6-O-triphenylmethyl-β-D-galactopyranoside 
• 139608-14-3 phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases

A trigalacturonic acid analogue carrying a cyclohexene framework in place of the central pyranose ring was synthesized as a molecular probe for the mechanistic investigation of endo-polygalacturonase 1 (endo-PG 1). Preliminary enzymatic studies revealed t

Synthesis of 3,6-branched arabinogalactan-type tetra- and hexasaccharides for characterization of monoclonal antibodies

Synthesis of tetra- and hexasaccharides built up from a β-(1→6)-linked galactopyranosyl backbone with arabinofuranosyl side chains at position 3 and with a 3-aminopropyl spacer related to arabinogalactans is described. These oligosaccharides were prepared

Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions

(Chemical Equation Presented) The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate 3H4 and

Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling

Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

Divergent synthesis of sialylated glycan chains: Combined use of polymer support, resin capture-release, and chemoenzymatic strategies

(Chemical Equation Presented) Carbo loading! The synthesis of α(2,3)- or α(2,6)-sialylated biantennary glycans is possible with a new approach. The common precursor 1 was synthesized with a soluble polymer support strategy (a) in combination with a resin capture-release protocol. Hexasaccharide 1 can then be diverged to various polysaccharides by enzymatic glycosylation (b). Bn = benzyl, TBS = tert-butyldimethylsilyl.

Prearranged glycosides. Part 8. Intramolecular α-galactosylation via succinoyl tethered glycosides

Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding α-(1→4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

Expeditious route to F unit building block of moenomycin A

Synthesis of the versatilely sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-β-D-galactopyranoside. The key synthetic steps included: (I) Regioselect

Synthesis of the two monomethyl esters of the disaccharide 4-O-α-D-galacturonosyl-D-galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences

Methyl (α-D-galactopyranosyluronic acid)-(1→4)-D-galactopyranuronate and methyl α-D-galactopyranosyluronate-(1→4)-D-galactopyranuronic acid have been synthesized by coupling methyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (3) or benzyl (benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (4) with benzyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate and methyl (phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate, respectively, using N-iodosuccinimide and trifluoromethanesulphonic acid as promoters, followed by removal of the benzyl groups. The 4'-OH unprotected dimers benzyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate and methyl (benzyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate were prepared from methyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate and benzyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate and acceptors 4 or 3, respectively. These compounds have been designed to serve as precursors for the preparation of higher-membered d-galacturonic acid oligomers methyl esterified in definite positions. Copyright (C) 1998 Elsevier Science Ltd.