274693-53-7

Usage

Uses

Used in Pharmaceutical Industry:
Carbamic acid, N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-, phenylmethyl ester is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable intermediate in the development of new drugs with improved efficacy and selectivity.
Used in Synthesis of Ticagrelor:
Specifically, Carbamicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylmethyl ester has been utilized in the synthesis of the all-cis carbocyclic precursor of ticagrelor, an antiplatelet drug used to reduce the risk of heart attack and stroke in patients with acute coronary syndrome or a history of heart attack. The synthesis involves oxidation and stereoselective reduction sequences, highlighting the importance of this chiral building block in creating complex pharmaceutical molecules.

Upstream product

• 501-53-1 benzyl chloroformate 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 1392909-30-6 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol D-(-)-mandelate 
• 1392909-34-0 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol R-(-)-3-chloromandelate 
• 611-71-2 (R)-Mandelic Acid 
• 88756-83-6 (+/-)-1β-amino-2α,3α-O-isopropylidene-2α,3α,4β-cyclopentanetriol 
• 36468-53-8 β-D-ribofuranose 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 
• 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 
• 532-20-7 D-Ribose 
• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 

Downstream Products

• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 274693-54-8 benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate 
• 376608-75-2 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadiene[d][1,3]dioxolene-4-yl}oxy)ethanol 
• 376608-74-1 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 274693-55-9 [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 
• 274693-27-5 ticagrelor 
• 1381841-46-8 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl isobutyl carbonate 
• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 1381841-39-9 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl butyrate 
• 1402150-30-4 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol oxalate 
• 1402150-02-0 ethyl 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)acetate 
• 1402150-05-3 2-((3aR,4S,6R,6aS)-6-(7-((1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetic acid 
• 1402150-11-1 methyl 2-((1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyloxy)acetate 
• 1402150-23-5 2-(((3aS,4R,6S,6aR)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)tetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-6-yl)oxy)ethanol 

Relevant academic research and scientific papers

Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD2

The invention relates to a method for preparing an isomer impurity TGA of a key optically active intermediate TGAD2 with ticagrelor. The method is protected Cbz. The method has the advantages of simple and mild reaction conditions, convenient post-treatme

Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1

The invention relates to a method for preparing an isomer impurity TGA of a key optically active intermediate TGAD1 with ticagrelor. The method is protected Cbz. The method has the advantages of simple and mild reaction conditions, convenient post-treatme

For [...] novel intermediate and its preparation method

The invention discloses a novel intermediate of ticagrelor, i.e., a compound represented by a formula (I), and a preparation method thereof. The preparation method for the compound represented by the formula (I) comprises a step of subjecting a compound represented by a formula (II) or a proper salt of the compound represented by the formula (II) and a compound represented by a formula (III) to a substitution reaction, wherein R in the formulas represents substituted or unsubstituted benzyl and benzoyl groups. The invention further discloses a preparation method for a ticagrelor compound represented by a formula (A) from the novel intermediate, i.e., the compound represented by the formula (I). The method for preparing ticagrelor from the novel intermediate has the advantages of short reaction time, easy and convenient post-treatment, high yield and high product purity.

Synthesis method of ticagrelor intermediate

The invention relates to a synthesis method of a ticagrelor intermediate, and in particular relates to a synthesis method of (3aS, 4R, 6S, 6aR)-tetrahydrogen-6-hydroxy-2,2-dimethyl-cyclopentane[d][1,3]-dioxolane-4-benzyl carbamate. The synthesis method of a resolving agent used in the synthesis is simple, the raw material is cheap and easy to obtain, the recycling method is simple, and the prepared compound is high in optical purity, high in yield and suitable for industrial production.

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.

A PROCESS FOR THE PREPARATION OF BENZYL [(3AS,4R,6S,6AR)-6-HYDROXY-2,2- DIMETHYLTETRAHYDRO-3AH-CYCLOPENTA[D][1,3]DIOXOL]-4-YL]CARBAMATE AND INTERMEDIATES IN THE PROCESS

The present invention is directed to a process for the preparation of benzyl [(3a S,4R,6S,6a R)-6-hydroxy-2,2-dimethyltetrahydro-3a H-cyclopenta[d][1,3]dioxol-4- yl]carbamate (VI), (VI), to products of said process and the use thereof.

OPTICALLY ACTIVE SALTS OF (3AR,4S,6R,6AS)-6-AMINO-2,2-DIMETHYLTETRAHYDRO-3AH- CYCLOPENTA-[D] [1,3]DIOXOL-4-OL AND A METHOD OF THEIR PREPARATION

Diastereomeric salts of the compound of formula I with D-(-)-mandelic and R-(-)-3- chloromandelic acid, a method of for the preparation thereof and their use in the synthesis of the drug ticagrelor.

Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents

Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e.g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor.

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.

CYCLOPROPYL MODULATORS OF P2Y12 RECEPTOR

The present invention relates to new cyclopropyl modulators of P2Y12 receptor activity, pharmaceutical compositions thereof, and methods of use thereof.