155899-66-4

Basic information

• Product Name: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol
• Synonyms: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol;4H-Cyclopenta-1,3-dioxol-4-ol, 6-aminotetrahydro-2,2-dimethyl-, (3aR,4S,6R,6aS)-;(3aR,4S,6R,6aS)-6-aMino-2,2-diMethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol;6-AMinotetrahydro-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-ol;(3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine;Ticagrelor Related Compound 1 ((3aR, 4S, 6R, 6aS)-6-Aminotetrahydro-2,2-Dimethyl-4H-Cyclopenta-1.3-dioxol-4-ol);(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-ol;(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-…
• CAS NO: 155899-66-4
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.2096
• EINECS: 1308068-626-2
• Mol File: 155899-66-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 85-88℃
• Boiling Point: 288℃
• Flash Point: 128℃
• Appearance: /
• Density: 1.170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.03±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol(155899-66-4)
• EPA Substance Registry System: (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol(155899-66-4)

Safety Data

• Hazardous Substances Data: 155899-66-4(Hazardous Substances Data)

Usage

Uses

(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol was used to preapare AZD6140 as an orally active reversible P2Y12 receptor antagonist for prevention of thrombosis.

Upstream product

• 190517-38-5 (1S,4R,5S,6R)-2,3-oxazabicyclo[2.2.1]heptane-5,6-dioxy-isopropylidene 
• 77-76-9 2,2-dimethoxy-propane 
• 7129-41-1 6-oxabicyclo[3.1.0]hex-2-ene 
• 138946-55-1 (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol 
• 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 
• 10257-32-6 D-ribose 
• 78341-96-5 (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 81026-76-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 4137-56-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 532-20-7 D-Ribose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 

Downstream Products

• 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 
• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 220241-60-1 (3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 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 
• 220347-05-7 AR-C₁₂₄₉₁₀XX 
• 274693-49-1 (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-ol 
• 1381841-44-6 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) thyl carbonate 
• 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 
• 1381841-52-6 (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 butyrate 
• 1381841-55-9 (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 ethyl carbonate 

Relevant articles and documents

Rapid syntheses of either enantiomer of important carbocyclic nucleoside precursors

The syntheses of both enantiomers of aminocyclopentanetriol 1, a versatile carbocyclic nucleoside precursor, is reported utilizing an amino acid-derived acylnitroso Diels-Alder cycloaddition. The sequence is practical and proceeds in an overall yield of 36% from the D-alanine-derived hydroxamic acid. (C) 2000 Elsevier Science Ltd.

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.

Synthesis method of ticagrelor intermediate

The present invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of a ticagrelor key intermediate. A chemical synthesis method of ticagrelor key intermediate 2-[(3aR,4S,6R,6aS)-6- amino tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3- dioxolane-4-yl] oxy] ethanol is specially designed. The method uses (1R,4S)-4 (benzyloxy)-2-alkenyl cyclopentanecarboxylic acid as a starting material, and conducts the steps of amidation, olefin oxidation, cyclization, Hoffmann reaction, deprotection and etherification to obtain an object compound. The method has the advantages of cheap and available raw materials, simple process, easily operated reaction process and high yield, and is applicable for industrial mass production.

Synthesis of Aminocyclopentanetriol Derivatives

The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor. The present invention provides in particular a process for the preparation of a compound of formula V comprising: a) providing a compound of formula IV , and b) reducing the compound of formula IV with activated zinc in the presence of copper to give the compound of formula V.