66888-27-5

Upstream product

• 129905-50-6 2,3,4,5,6-penta-O-acetyl-1-chloro-S-phenyl-1-thio-L-galactitol 
• 1372792-90-9 1,2,3,4,5-penta-O-acetyl-6-O-benzyl-D-galactitol 
• 1372610-16-6 1,2,3,4,5-penta-O-acetyl-D-galactitol 
• 10257-28-0 D-Galactose 
• 54325-28-9 (3R,4S,5R,6R)-6-(trityloxymethyl)tetrahydropyran-2,3,4,5-tetrol 
• 108-24-7 acetic anhydride 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 
• 72003-68-0 2,3,4,5,6-penta-O-acetyl-D-galactose diethyl dithioacetal 
• 129941-51-1 1,2,3,4,5-penta-O-acetyl-6-S-phenyl-6-thio-D-galactitol 
• 128333-82-4 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-L-galacto-hept-1-enitol 

Downstream Products

• 7404-37-7 penta-O-acetyl-aldehydo-D-mannose semicarbazone 
• 3427-23-4 2,3-Dideoxy-1-C-p-nitrophenyl-D-manno-oct-2-en-1-ulose-pentaacetat 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 187269-57-4 1,6-bis-[3-(3-carbomethoxymethylphenyl)-4-(tetra-O-acetyl-α-D-mannopyranosyl)oxyphenyl]hexane 
• 187269-88-1 1,4-bis-[3-(3-carbomethoxymethylphenyl)-4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]butane 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-L-galactopyranose 
• 15572-79-9 aldehydo-L-Galactose 
• 89243-20-9 1',1'-bis<3-methyl-5-oxo-1-phenyl-Δ²-4-pyrazyl>-1'-deoxy-2',3',4',5',6'-penta-O-acetyl-D-glucitol 
• 1118624-81-9 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 63629-73-2 (+)-3-acetyl-2-(D-manno-penta-acetoxypentyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 243120-94-7 4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside 
• 243120-93-6 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside 
• 187269-63-2 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride 
• 28541-77-7 4-bromophenyl α-D-mannopyranoside 

Relevant academic research and scientific papers

Efficient synthesis of L-galactose from D-galactose

Racemic protein crystallography is an emerging methodology to obtain high-resolution protein structures. Preparation of both a mirror image of protein and a mirror image of glycan is essential to apply the new methodology to glycoprotein. This article describes an efficient synthesis of L-galactose that is amirror image of D-galactose. The developed method takes only 6 steps from D-galactose without any chromatographic purification.

Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives

Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from d-galactose, d-glucose, d-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac 2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO 6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%.

1,2;3,4-Di-O-isopropylidene-l-galactose synthesis from its d-enantiomer

Easy procedure was devised to obtain di-O-isopropylidene-l-galactose from di-O-isopropylidene-d-galactose.

Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses

Methyl 6-S-phenyl-6-thio-α-D-glucopyranoside, prepared in high yield from methyl α-D-glucopyranoside by the action of diphenyl sulfide and tributylphosphine in pyridine, was converted into 6-S-phenyl-6-thio-D-glucitol pentaacetate (7) by sequential hydrolysis, borohydride reduction, and acetylation.Oxidation of 7 with 3-chloroperoxybenzoic acid gave the corresponding S-epimeric sulfoxides, which underwent Pummerer rearrangement to 1-epimeric L-gulose S-phenyl monothiohemiacetal hexaacetates.Boron trifluoride-catalyzed reaction of the latter with thiophenol gave theanalogues diphenyl dithioacetal, whereas base-catalyzed methanolysis led to free L-gulose.Treatment of 7 with N-chlorosuccinimide afforded 1-epimeric 1-chloro-1-S-phenyl-1-thio-L-gulitol pentaacetates, which were hydrolyzed to provide aldehydo-L-gulose pentaacetate.The same reaction sequences were performed with 6-S-phenyl-6-thio-D-galactose, synthesized in two steps from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, furnishing ultimately L-galactose, its diphenyl dithioacetal pentaacetate, and aldehydo-L-galactose pentaacetate.Similar reaction sequences for the chain-terminal interchange of oxidation state in other ω-S-phenyl-ω-thioaldoses may prove useful for the preparation of less-common sugar derivatives.

1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose

The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.