3254-17-9

Usage

Uses

Used in Organic Synthesis:
3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate) is used as an intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate) is used as a key compound in the development of novel drug candidates. Its ability to be modified and functionalized allows for the creation of new molecules with potential therapeutic properties, contributing to the advancement of drug discovery and development.
Used in Chemical Research:
3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate) is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its unique structure provides opportunities for researchers to investigate new methods and techniques in organic chemistry, further expanding the knowledge base in this field.

InChI:InChI=1/C16H24O10/c1-6-21-16(5)25-14-13(23-10(4)19)12(22-9(3)18)11(7-20-8(2)17)24-15(14)26-16/h11-15H,6-7H2,1-5H3/t11?,12-,13+,14+,15-,16?/m1/s1

Upstream product

• 64-17-5 ethanol 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 

Downstream Products

• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 38430-69-2 O²,O³,O⁴,O⁶-Tetraacetyl-O¹-benzoyl-β-D-glucopyranose 
• 61081-62-7 2,3,4,6-tetra-O-acetyl-1-O-(acetylsalicylyl)-β-D-glucopyranose 
• 302799-52-6 (3aR,5R,6R,7S,7aR)-6,7-Bis-(4-chloro-benzyloxy)-5-(4-chloro-benzyloxymethyl)-2-ethoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 
• 51532-76-4 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 40246-33-1 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 98906-49-1 methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 98906-48-0 methyl 2-O-acetyl-3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-1→4-(2,3,6-tri-O-benzyl)-β-D-glucopyranoside 
• 213028-88-7 1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 
• 153947-47-8 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 213028-97-8 6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant academic research and scientific papers

Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana

First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of 1H-NMR, 13C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs' inhibitory activity of Raddeanin A may contribute to its cytotoxicity.

Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid

The endofungal metabolite epicoccamide D was synthesised in eighteen steps and 17 % yield as the first member of the family of natural glycotetramic acids. The modular character of the synthesis opens access also to analogues featuring different sugars and spacers. It comprises several high-yielding key steps. The β-D-mannosyl group was introduced by using an α-D-glucosyl imidate donor with subsequent oxidative-reductive epimerisation at C-2′. The pyrrolidine ring was closed quantitatively by a Lacey-Dieckmann condensation of an N-(β-ketoacyl)-N-methyl alaninate. The resulting 3-[ω-(β-D- mannosyl)octadec-2-enoyl]tetramic acid was hydrogenated in the presence of the rhodium catalyst (R,R)-[Rh(Et-DUPHOS)][BF4] to establish the (7S)-stereocentre. This was possible only after blocking the acyltetramic acid as a BF2-chelate to prevent capture of the metal catalyst. We also assigned the hitherto unknown configuration of the natural product as being 5S,7S by comparison of its 13C NMR spectroscopic and optical rotation data with those of our two synthetic 5S,7R/S-diasteromers. Copyright

An environmentally benign and practical synthesis of sugar orthoesters promoted by potassium fluoride

An extremely practical method for synthesis of sugar orthoesters has been developed without using any organic amines or heavy metals as additives. Various sugar orthoesters were prepared in good yields by the reaction of an acylated glycosyl bromide and a

Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH

Peracetylated sugars can be efficiently converted into the corresponding 1,2-ethylidenes, -orthoesters, and -glycals via the in situ generation of glycosyl iodides promoted by I2/Et3SiH. The approach is straightforward and avoids isolation of the sensitive iodinated intermediates.

ONE-POT SYNTHESIS OF SUBSTITUTED ALLYL-α-D-GLUCOPYRANOSIDES BY AN in situ ANOMERIZATION PROTOCOL

A new 3-step, 1-pot procedure for the stereoselective α-glycosylation of substituted allylic alcohols has been developed.The key step involves an in situ anomerization of the β-glycoside, obtained by Schmidt's glycosylation method, upon treatment with TiCl4.