1,2,3,4,6-Penta-O-acetyl-D-galactopyranose - CAS 25878-60-8
Category: Carbohydrates
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1.Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine.
Sakee U1, Nasuk C. Carbohydr Res. 2010 Jun 16;345(9):1222-4. doi: 10.1016/j.carres.2010.03.040. Epub 2010 Apr 8.
A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Boc-groups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate-ethylenediamine C-glycosyl chelators.
2.Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses.
Santoyo González F1, Baer HH. Carbohydr Res. 1990 Jul 15;202:33-47.
Methyl 6-S-phenyl-6-thio-a-D-glucopyranoside, prepared in high yield from methyl a-D-glucopyranoside by the action of diphenyl disulfide 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 the analogous 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-a-D-galactopyranose, furnishing ultimately L-galactose, its diphenyl dithioacetal pentaacetate, and aldehydo-L-galactose pentaacetate.
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CAS 25878-60-8 1,2,3,4,6-Penta-O-acetyl-D-galactopyranose

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