6763-46-8

Usage

Uses

Used in Pharmaceutical Industry:
[(2R,3S,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxo-hexan-3-yl] acetate is used as a key reagent in the synthesis of various pharmaceuticals. Its unique molecular structure allows for the creation of a wide range of medicinal compounds, making it a valuable asset in the development of new drugs.
Used in Organic Synthesis:
In the field of organic chemistry, [(2R,3S,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxo-hexan-3-yl] acetate serves as an essential building block for the synthesis of various organic compounds. Its versatile structure enables the formation of a diverse array of molecules, contributing to the advancement of organic chemistry research and development.
Used in Research and Development:
Due to its complex molecular structure and potential applications, [(2R,3S,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxo-hexan-3-yl] acetate is also employed in research and development settings. Scientists and researchers utilize [(2R,3S,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxo-hexan-3-yl] acetate to explore new chemical reactions, investigate its properties, and develop innovative applications in various industries.

InChI:InChI=1/C8H14O8/c1-4(11)15-16-6(3-10)8(14)7(13)5(12)2-9/h3,5-9,12-14H,2H2,1H3/t5-,6+,7+,8-/m1/s1

Upstream product

• 128333-82-4 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-L-galacto-hept-1-enitol 
• 129905-50-6 2,3,4,5,6-penta-O-acetyl-1-chloro-S-phenyl-1-thio-L-galactitol 
• 129941-51-1 1,2,3,4,5-penta-O-acetyl-6-S-phenyl-6-thio-D-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 
• 72003-68-0 2,3,4,5,6-penta-O-acetyl-D-galactose diethyl dithioacetal 
• 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 

Downstream Products

• 5456-68-8 penta-O-acetyl-keto-D-galacto-1,2-dideoxy-[3]octulose 
• 112070-67-4 4-chloro-benzenesulfonic acid-(penta-O-acetyl-D-galactitol-1-ylidenehydrazide) 
• 13485-47-7 2,3-Dideoxy-1-C-(3,4-dimethoxy-phenyl)-D-galacto-oct-2-en-1-ulose-pentaacetat 
• 13035-34-2 2,3-Dideoxy-1-C-(2,3,4-trimethoxy-phenyl)-D-galacto-oct-2-en-1-ulose-pentaacetat 
• 3075-43-2 1-C-(p-Ethoxy-phenyl)-2,3-dehydro-2,3-didesoxy-4,5,6,7,8-penta-O-acetyl-D-galacto-1-octose 
• 114192-66-4 penta-O-acetyl-aldehydo-D-galactose 2-methoxybenzoylhydrazone 
• 75759-74-9 3-((E)-(3S,4R,5S,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-phenyl-benzo[f]quinolinium; iodide 
• 75759-76-1 3-((E)-(3S,4R,5S,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-p-tolyl-benzo[f]quinolinium; iodide 
• 5151-97-3 penta-O-acetyl-aldehydo-D-galactose benzoylhydrazone 
• 85193-81-3 2,3,4,5-penta-O-acetyl-aldehydo-D-galactose (2,4-dichlorophenoxyacetyl)hydrazone 
• 849585-22-4 LACTIC ACID 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 28512-68-7 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 36868-85-6 4-chlorophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 

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.