866551-95-3

Basic information

• Product Name: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester
• Synonyms: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester;Ethyl 2-(((3aR,4S,6R,6aS)-6-(((benzyloxy)carbonyl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)acetate
• CAS NO: 866551-95-3
• Molecular Formula: C20H27NO7
• Molecular Weight: 393.43088
• Mol File: 866551-95-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 540.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 11.26±0.60(Predicted)
• CAS DataBase Reference: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester(866551-95-3)
• EPA Substance Registry System: Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester(866551-95-3)

Safety Data

• Hazardous Substances Data: 866551-95-3(Hazardous Substances Data)

Usage

Uses

Ethyl 2-[[(3aR,4S,6R,6aS)-6-[(Benzyloxycarbonyl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate is used as a reactant in the synthesis of Ticagrelor (T437700), a platelet aggregation inhibitor.

Upstream product

• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 105-36-2 ethyl bromoacetate 
• 501-53-1 benzyl chloroformate 
• 188434-69-7 (1R,4S)-4-(benzyloxy)cyclopent-2-en-1-yl acetate 
• 1423769-48-5 benzyl ((3aS,4R,6aS)-2,2-dimethyl-6-oxotetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate 
• 274693-53-7 [3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester 
• 1423769-49-6 benzyl ((3aS,4R,6R,6aR)-6-hydroxy-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate 
• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 36468-53-8 β-D-ribofuranose 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 155855-51-9 tetrahydro-2,2-dimethyl-6-phenylmethyl-(3aS,4S,7R,7aS)-4,7-methano-4H-1,3-dioxolo[4,5-d][1,2]oxazine 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 

Downstream Products

• 1402150-32-6 (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol 

Relevant articles and documents

Synthesis of an all-cis intermediate of ticagrelor

A six step conversion of the common carbocyclic nucleoside precursor 8 into the all-cis key intermediate for the synthesis of ticagrelor analogs is reported. The method involves two oxidation/stereoselective reduction sequences for both the C-O and C-N bonds. Inversion of stereochemistry was confirmed by analysis of spin couplings between the hydrogens at the junction of the 1,3-dioxolane and cyclopentane rings.

Method for preparing ticagrelor key intermediate

The invention relates to a chemical synthesis method of ticagrelor key intermediate 2-[[(3aR, 4S, 6R, 6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxolane-4-yl] oxy]ethanol (a key intermediate A). The method comprises the following steps: taking D-ribose as a raw material, and carrying out ten chemical reaction steps of 1-locus methylation and 2,3-loci isopropylidene protection, 4-locus derivatization, iodination, furan ring-opening, hydroxylamine reaction, palladium on carbon catalytic hydrogenation, amino Cbz protection, hydroxy protection, sodium borohydride reduction ester, Cbz removal protection and the like, thereby obtaining the key intermediate A. The raw materials are cheap and readily available, the preparation process is high in operability, steps of optical resolution, chiral induction and the like are avoided, the total yield is relatively high, and the product quality is better; particularly due to the use of sodium borohydride reduction ester, the preparation cost of ticagrelor is greatly reduced; and the method is suitable for large-scale industrial production.

NEW INTERMEDIATES AND PROCESSES FOR PREPARING TICAGRELOR

The present invention is related to new intermediates and processes for preparing Ticagrelor disclosed in this patent application.