3254-17-9

Basic information

• Product Name: 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate)
• Synonyms: 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate);1,2-O-(1-Ethoxyethylidene)-α-D-glucopyranose Triacetate;1,2-O-Ethylorthoacetyl-α-D-glucopyranose Triacetate
• CAS NO: 3254-17-9
• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.35576
• Product Categories: Carbohydrates & Derivatives
• Mol File: 3254-17-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 432.174°C at 760 mmHg
• Flash Point: 187.536°C
• Appearance: /
• Density: 1.289g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate)(3254-17-9)
• EPA Substance Registry System: 3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate)(3254-17-9)

Safety Data

• Hazardous Substances Data: 3254-17-9(Hazardous Substances Data)

Usage

Uses

3,4,6-Tri-O-acetyl-α-D-Glucopyranose 1,2-(Ethyl Orthoacetate) (cas# 3254-17-9) is a compound useful in organic synthesis.

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

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 

Relevant articles and documents

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

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.