120085-63-4

Basic information

• Product Name: 4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE,
• Synonyms: 4,5,7,-Tri-o-acetyl-2,6-anhyro-3-deoxy-D-lyxo-hept-2-enononitrile;[(2R,3R,4R)-4-Acetyloxy-2-(acetyloxymethyl)-6-cyano-3;4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-D-lyxo-hept-2-enononitrile
• CAS NO: 120085-63-4
• Molecular Formula: C13H15NO7
• Molecular Weight: 297.262
• Mol File: 120085-63-4.mol

Chemical Properties

• Boiling Point: 397.8oC at 760 mmHg
• Flash Point: 174oC
• Appearance: /
• Density: 1.29g/cm3
• Vapor Pressure: 1.54E-06mmHg at 25°C
• Refractive Index: 1.497
• CAS DataBase Reference: 4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE,(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE,(120085-63-4)
• EPA Substance Registry System: 4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE,(120085-63-4)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 120085-63-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE is used as an intermediate in the production of various drugs and medications. Its unique chemical structure and properties make it a valuable building block in the synthesis of complex organic molecules, contributing to the development of new pharmaceuticals.
Used in Chemical Research:
4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE, is used as a research tool in organic synthesis, allowing scientists to explore its properties and potential applications in various chemical reactions and processes.
Used in Agriculture:
4,5,7-TRI-O-ACETYL-2,6-ANHYDRO-3-DEOXY-D-LYXO-HEPT-2-ENONONITRILE has potential applications in the field of agriculture, where its unique chemical properties can be harnessed for various purposes, such as the development of new agrochemicals or the improvement of crop protection strategies.
Used in Materials Science:
In the field of materials science, this compound may be utilized for the development of new materials with specific properties, such as improved strength, durability, or functionality, thanks to its unique chemical structure and properties.

InChI:InChI=1/C13H15NO7/c1-7(15)18-6-12-13(20-9(3)17)11(19-8(2)16)4-10(5-14)21-12/h4,11-13H,6H2,1-3H3/t11-,12-,13-/m1/s1

Upstream product

• 83497-42-1 2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide 
• 52443-07-9 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile 

Downstream Products

• 180336-28-1 methyl C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formimidate 
• 183233-11-6 Acetic acid (2R,3R,4R)-4-acetoxy-2-acetoxymethyl-6-carbamoyl-3,4-dihydro-2H-pyran-3-yl ester 
• 180336-29-2 C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formamidine hydrochloride 

Relevant articles and documents

The first synthesis of 3-deoxy-D-lyxo-2-heptulosaric acid (DHA) derivatives

Synthetic route to the methyl ester of methyl glycoside of 3-deoxy-D-lyxco-heptulosaric acid (13) starting from 1-cyanogalactal 2 is described. The latter substance was prepared by direct elimination of acetic acid from 1 using 1,8-diazabicyclo[5.4.0]unde

Zinc-N-base mediated synthesis of pyranoid glycals mechanistic studies

Reactions of acetobromoglucose 1 or acetylated 1-bromo-D-galactopyranosyl cyanide 3 with zinc dust in the presence of a N-base (1-methylimidazole, 4-methylpyridine, or triethylamine, pyridine, respectively) in ethyl acetate or benzene were efficiently inhibited by 10-30 mol % of 1,4-dinitrobenzene, elemental sulfur, or carbon tetrachloride. Presence of glycosyl radicals in these reactions was also shown by trapping them with tert-dodecyl mercaptan or methyl acrylate. Based on these observations and the high yielding formation of glycal derivatives 2 and 4 of high purity a free radical chain mechanism is proposed for the transformations.

Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles

Acetylated 1-cyanoglycals (2,6-anhydro-3-deoxyhept/hex-2-enonitriles) were prepared by direct elimination of acetic acid from the appropriate acetylated 2,6-anhydrohept/hexononitriles with 1,8-diazabicycloundec-7-ene (DBU) in aprotic solvents.Heterocyclisation of the cyano group of acetylated 1-cyano-D-galactal with 2-aminothiophenol led to 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)benzothiazole.Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazoles with DBU. 3-(Per-O-acetylhexo/pentopyranosyl)-triazolopyrimidines rearranged with DBU to the corresponding acetylated 2-glycosyl-triazolopyrimidines.By the reaction of 1-cyano-D-galactal with ammonium azide, 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)tetrazole was prepared and then transformed with carboxylic acid derivatives into 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)-4-substituted-1,3,4-oxadiazoles.

Preparation of 2,6-Anhydro-3-deoxyhept-(or hex-)2-enononitriles (1-Cyanoglycals) from 1-Bromo-D-glycosyl Cyanides with Zinc under Aprotic Conditions

Acetylated 1-bromo-D-glycosyl cyanides 1 - 5 react with zinc dust in acetic acid, acetic acid/water, or 2-propanol to give mixtures of acetylated 1-cyanoglycals 6-9 and anomeric pairs of glycosyl cyanides 10-14.Reaction of 1-5 in refluxing benzene in the presence of one equivalent of triethylamine or especially pyridine predominantly leads to the formation of 1-cyanoglycals.