124477-08-3

Upstream product

• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 818-08-6 di(n-butyl)tin oxide 
• 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 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 196876-47-8 phenyl 3-O-benzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 124477-09-4 Dithiocarbonic acid O-((2S,4aR,6S,7R,8S,8aS)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester S-methyl ester 
• 670249-31-7 phenyl 3-benzyl-4,6-O-benzylidene-2-O-pivaloyl-1-thio-β-D-galactopyranoside 
• 819798-05-5 phenyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-1-thio-β-D-galactopyranoside 
• 124579-04-0 1,5-anhydro-3-O-benzyl-4,6-O-benzyl-idene-2-deoxy-D-lyxo-hex-1-enitol 
• 917568-59-3 phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 917568-60-6 phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide 
• 917568-43-5 2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate S-oxide 
• 917568-42-4 2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate 
• 917568-41-3 phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranosiduronic acid 
• 917568-40-2 phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 196876-49-0 phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides

This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll

Highly Efficient Selective Benzylation of Carbohydrates Catalyzed by Iron(III) with Silver Oxide and Bromide Anion as Co-catalysts

A highly efficient, green, and regioselective method for the benzylation of diols and polyols was developed. With the use of Ag2O (0.6 equiv.) and tetrabutylammonium bromide (0.1 equiv.) as co-catalysts, the iron(III)-catalyzed benzylation reaction proceeded to completion at 40 °C within 2–3 h and gave the products in high yields with high regioselectivities. A mechanism involving the principle of enhanced basicity of Ag2O by soft anions was proposed.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

Dimethyltin Dichloride Catalyzed Regioselective Alkylation of cis-1,2-Diols at Room Temperature

Here, we have developed a mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and

Synthesis of oligosaccharides corresponding to the polysaccharides of Lactobacillus and Thermophilus strains

Synthesis of a branched trisaccharide and a tetrasaccharide repeating units corresponding to the polysaccharides of Lactobacillus spp. G-77 and Thermus thermophilus Samu-SA1 as their methyl glycosides has been achieved in excellent yield. Most of the glycosyl linkages are 1,2-cis in these oligosaccharide fragments. Georg Thieme Verlag Stuttgart.

The total synthesis of moenomycin A

Moenomycin A is the only known natural antibiotic that inhibits bacterial cell wall synthesis by binding to the transglycosylases that catalyze formation of the carbohydrate chains of peptidoglycan. We report here the total synthesis of moenomycin A using

Nickel(II) chloride-mediated regioselective benzylation and benzoylation of diequatorial vicinal diols

Ni(II)-chelates of monosaccharide vicinal diols were found to be useful intermediates in regioselective monobenzylation and monobenzoylation. It was observed that the substitution occurs exclusively at the position adjacent to the axially oriented substit

Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors

Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.

PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES

Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus