274693-53-7

Basic information

• Product Name: CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester
• Synonyms: CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester;N-[(3aS,4R,6S,6aR)-Tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamicacid phenylmethyl ester;N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester;((3AS 4R 6S 6AR)6-HYDROXY-2,2-DIMETHYL-TETRAHYDROCYCLOPENTA(1,3)DIOXOL 4,YL)CARBAMIC ACID BENZYL ESTER;Benzyl((3aS, 4R, 6S, 6aR)-6-hydroxy-2,2-diMethyltetrahydro-3aH-cyclopenta[1,3]-dioxol-4yl)carbaMate;CarbaMic acid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-;benzyl N-[(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]carbamate;benzyl((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate
• CAS NO: 274693-53-7
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.35
• EINECS: 1308068-626-2
• Mol File: 274693-53-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 489.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.28
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 11.41±0.60(Predicted)
• CAS DataBase Reference: CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester(274693-53-7)
• EPA Substance Registry System: CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester(274693-53-7)

Safety Data

• Hazardous Substances Data: 274693-53-7(Hazardous Substances Data)

Usage

Uses

Phenylmethyl ester N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamic acid is a useful chiral building block. It has been used in the synthesis of all-cis carbocyclic precursor of ticagrelor via oxidation/stereoselective reduction sequences.

Upstream product

• 501-53-1 benzyl chloroformate 
• 1413395-24-0 (3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-aminium (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 88756-83-6 (+/-)-1β-amino-2α,3α-O-isopropylidene-2α,3α,4β-cyclopentanetriol 
• 611-71-2 (R)-Mandelic Acid 
• 1392909-34-0 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol R-(-)-3-chloromandelate 
• 1392909-30-6 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol D-(-)-mandelate 
• 155899-66-4 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 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 
• 532-20-7 D-Ribose 

Downstream Products

• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 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 
• 274693-54-8 benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate 
• 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 
• 376608-65-0 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid 

Relevant articles and documents

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

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.

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.