Ticagrelor Intermediate1 supplier

Name
1-Acetyladamantane Intermediate
EINECS 1312995-182-4
CAS No. 274693-55-9
Article Data17
CAS DataBase
Density 1.21 g/cm³
Solubility
Melting Point
Formula C₁₀H₁₉NO₄
Boiling Point 338.144 °C at 760 mmHg
Molecular Weight 217.265
Flash Point 158.304 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Ticagrelor Intermediate1;
PSA 73.94000
LogP 0.31530

Synthetic route

: 274693-54-8
benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	99%
With 5%-palladium/activated carbon In methanol at 20℃; for 1h;	75.7%
palladium on charcoal In ethanol

: C17H25NO4

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethanol at 50 - 60℃; under 750.075 Torr; for 12h; Autoclave; Inert atmosphere;	98%
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 20℃; under 3750.38 - 6000.6 Torr; for 10h;	92.8%

: C10H16O5

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With hydrogenchloride; pyridoxal 5'-phosphate; isopropylamine; triethylamine In water at 25℃; for 16h; pH=8; Solvent; Reagent/catalyst; Temperature; Large scale; Enzymatic reaction;	97%

: C15H27NO6

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
In ethylene glycol at 120℃; for 8h; Solvent; Temperature;	92%

: C17H24N2O6

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 20℃; for 14h;	91.5%

: 1444301-50-1
(3aS,4R,6S,6aR)-N-benzyl-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 40℃; under 7500.75 Torr; for 168h;	63%

: 345898-95-5
N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 4.2: 3 h / 20 °C 5.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 6.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 5 h / Reflux 2.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 3.2: 4 h / 0 - 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme
Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide / 2 h / Reflux 2.1: ammonium formate; palladium 10% on activated carbon / methanol / 1.5 h / Reflux 3.1: potassium carbonate / water / 5.5 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C 4.2: 6.33 h / -20 - 20 °C 5.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C 6.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C View Scheme

: ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 2: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C 1.2: 20 °C 1.3: pH 6 - 7 2.1: ammonium formate / palladium 10% on activated carbon / ethanol / 30 - 70 °C View Scheme

: 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

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 1.2: 3 h / 20 °C 2.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 3.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 °C 2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C 2.2: 20 °C 2.3: pH 6 - 7 3.1: ammonium formate / palladium 10% on activated carbon / ethanol / 30 - 70 °C View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate 2: hydrogen / palladium on activated charcoal / ethanol View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C 1.2: 6.33 h / -20 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C 3.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C View Scheme

: 4099-85-8, 5531-21-5, 20672-63-3, 20672-65-5, 58763-00-1, 63029-07-2, 72402-14-3, 84894-45-1, 129263-68-9
methyl 2,3-O-isopropylidene-D-ribofuranoside

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: pyridine / 24 h / 20 °C 2.1: sodium iodide / butanone / 24 h / 120 °C 3.1: zinc / ethanol / 1 h / 70 °C 4.1: sodium carbonate / ethanol / 1 h / 50 °C 5.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 6.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 8.2: 3 h / 20 °C 9.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 10.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: pyridine / 4 h / -10 - -5 °C 2.1: lithium bromide / butanone / 22 h / 80 °C 3.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 4.1: sodium carbonate / methanol / 0.5 h / 25 °C 5.1: toluene / 5 h / Reflux 6.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 7.2: 4 h / 0 - 20 °C / Inert atmosphere 8.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 10 steps
1.1: pyridine / 24 h / 20 °C
2.1: sodium iodide / butanone / 24 h / 120 °C
3.1: zinc / ethanol / 1 h / 70 °C
4.1: sodium carbonate / ethanol / 1 h / 50 °C
5.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
8.2: 3 h / 20 °C
9.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
10.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: pyridine / 4 h / -10 - -5 °C
2.1: lithium bromide / butanone / 22 h / 80 °C
3.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
4.1: sodium carbonate / methanol / 0.5 h / 25 °C
5.1: toluene / 5 h / Reflux
6.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
7.2: 4 h / 0 - 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

: 532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7
D-Ribose

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: perchloric acid / acetone / 24 h / Molecular sieve 2.1: pyridine / 24 h / 20 °C 3.1: sodium iodide / butanone / 24 h / 120 °C 4.1: zinc / ethanol / 1 h / 70 °C 5.1: sodium carbonate / ethanol / 1 h / 50 °C 6.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 7.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 9.2: 3 h / 20 °C 10.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 11.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: perchloric acid / acetone / 24 h / Molecular sieve
2.1: pyridine / 24 h / 20 °C
3.1: sodium iodide / butanone / 24 h / 120 °C
4.1: zinc / ethanol / 1 h / 70 °C
5.1: sodium carbonate / ethanol / 1 h / 50 °C
6.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
7.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
9.2: 3 h / 20 °C
10.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
11.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme

: 4137-56-8, 5531-22-6, 6953-71-5, 52631-00-2, 63087-95-6, 84894-43-9, 13007-50-6
((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium iodide / butanone / 24 h / 120 °C 2.1: zinc / ethanol / 1 h / 70 °C 3.1: sodium carbonate / ethanol / 1 h / 50 °C 4.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 5.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 7.2: 3 h / 20 °C 8.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 9.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: lithium bromide / butanone / 22 h / 80 °C 2.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 3.1: sodium carbonate / methanol / 0.5 h / 25 °C 4.1: toluene / 5 h / Reflux 5.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 6.2: 4 h / 0 - 20 °C / Inert atmosphere 7.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium iodide / butanone / 24 h / 120 °C
2.1: zinc / ethanol / 1 h / 70 °C
3.1: sodium carbonate / ethanol / 1 h / 50 °C
4.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
7.2: 3 h / 20 °C
8.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
9.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme

Multi-step reaction with 7 steps
1.1: lithium bromide / butanone / 22 h / 80 °C
2.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
3.1: sodium carbonate / methanol / 0.5 h / 25 °C
4.1: toluene / 5 h / Reflux
5.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
6.2: 4 h / 0 - 20 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

: 155934-55-7
(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium carbonate / ethanol / 1 h / 50 °C 2.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 5.2: 3 h / 20 °C 6.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 7.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium carbonate / methanol / 0.5 h / 25 °C 2.1: toluene / 5 h / Reflux 3.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 4.2: 4 h / 0 - 20 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium carbonate / ethanol / 1 h / 50 °C
2.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
5.2: 3 h / 20 °C
6.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
7.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme

Multi-step reaction with 5 steps
1.1: sodium carbonate / methanol / 0.5 h / 25 °C
2.1: toluene / 5 h / Reflux
3.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
4.2: 4 h / 0 - 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

: 155899-66-4
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 2.2: 3 h / 20 °C 3.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 4.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / ethanol; water / 3 h / 60 - 65 °C 1.2: 0.25 h 2.1: sodium t-butanolate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / -10 - 5 °C 3.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 3.2: 0.25 h 4.1: hydrogen / 20% palladium hydroxide-activated charcoal / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: sodium carbonate / water; 4-methyl-2-pentanone / 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0 °C 3.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C 3.2: 20 °C 3.3: pH 6 - 7 4.1: ammonium formate / palladium 10% on activated carbon / ethanol / 30 - 70 °C View Scheme

: 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

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 3.2: 3 h / 20 °C 4.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 5.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 4 h / 0 - 20 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

: 50600-40-3
(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: zinc / ethanol / 1 h / 70 °C 2.1: sodium carbonate / ethanol / 1 h / 50 °C 3.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 6.2: 3 h / 20 °C 7.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 8.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: zinc / ethanol / 1 h / 70 °C
2.1: sodium carbonate / ethanol / 1 h / 50 °C
3.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
6.2: 3 h / 20 °C
7.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
8.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme

: 1383715-55-6
(3aR,4S,6R,6aS)-6-(N,N-dibenzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium t-butanolate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / -10 - 5 °C 2.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 2.2: 0.25 h 3.1: hydrogen / 20% palladium hydroxide-activated charcoal / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / dichloromethane; tetrahydrofuran / 5.5 h / 0 - 5 °C 2.1: hydrogen / palladium-on-charcoal / ethanol / 14 h / 43 - 48 °C / 3620.13 Torr / Autoclave 3.1: lithium borohydride / dichloromethane / 24 h / 20 - 25 °C / Inert atmosphere 3.2: 0.25 h 3.3: 0.5 h View Scheme
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / dichloromethane; tetrahydrofuran / 5.5 h / 0 - 5 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol-d6 / 14 h / 43 - 48 °C / 3620.13 Torr / Inert atmosphere 2.2: -5 - 55 °C 3.1: potassium carbonate / water; dichloromethane / 20 - 25 °C / pH 10 - 10.5 4.1: lithium borohydride / dichloromethane / 24 h / 20 - 25 °C / pH 10 - 10.5 / Inert atmosphere View Scheme

: 1383715-56-7
tert-butyl [[(3aR,4S,6R,6aS)-6-(N,N-dibenzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C 1.2: 0.25 h 2.1: hydrogen / 20% palladium hydroxide-activated charcoal / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen / palladium-on-charcoal / ethanol / 14 h / 43 - 48 °C / 3620.13 Torr / Autoclave 2.1: lithium borohydride / dichloromethane / 24 h / 20 - 25 °C / Inert atmosphere 2.2: 0.25 h 2.3: 0.5 h View Scheme
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol-d6 / 14 h / 43 - 48 °C / 3620.13 Torr / Inert atmosphere 1.2: -5 - 55 °C 2.1: potassium carbonate / water; dichloromethane / 20 - 25 °C / pH 10 - 10.5 3.1: lithium borohydride / dichloromethane / 24 h / 20 - 25 °C / pH 10 - 10.5 / Inert atmosphere View Scheme

: 1383715-57-8
2-[[(3aR,4S,6R,6aS)-6-(N,N-dibenzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]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

Conditions

Conditions	Yield
With hydrogen; 20% palladium hydroxide-activated charcoal In methanol at 20 - 25℃; under 2327.23 Torr; for 10h; Autoclave; Inert atmosphere;

: 88756-83-6
(+/-)-1β-amino-2α,3α-O-isopropylidene-2α,3α,4β-cyclopentanetriol

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanol / 20 °C / Reflux; Resolution of racemate 2: potassium carbonate / water; 4-methyl-2-pentanone 3: potassium tert-butylate 4: hydrogen / palladium on activated charcoal / ethanol View Scheme
Multi-step reaction with 4 steps 1: ethanol / 20 °C / Reflux; Resolution of racemate 2: potassium carbonate / water; 4-methyl-2-pentanone 3: potassium tert-butylate 4: hydrogen / palladium on activated charcoal / ethanol View Scheme

: 1392909-30-6
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol D-(-)-mandelate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / water; 4-methyl-2-pentanone 2: potassium tert-butylate 3: hydrogen / palladium on activated charcoal / ethanol View Scheme

: 1392909-34-0
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta-[d][1,3]dioxol-4-ol R-(-)-3-chloromandelate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / water; 4-methyl-2-pentanone 2: potassium tert-butylate 3: hydrogen / palladium on activated charcoal / ethanol View Scheme

: 1416158-39-8
tert-butyl [[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Stage #1: tert-butyl [[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate With lithium borohydride In dichloromethane at 20 - 25℃; for 24h; Inert atmosphere; Stage #2: With acetic acid In dichloromethane for 0.25h; Stage #3: With potassium carbonate In dichloromethane for 0.5h;
With lithium borohydride In dichloromethane at 20 - 25℃; for 24h; pH=10 - 10.5; Inert atmosphere;	0.7 g

: 78341-96-5
(3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 2.1: sodium carbonate / methanol / 0.5 h / 25 °C 3.1: toluene / 5 h / Reflux 4.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 5.2: 4 h / 0 - 20 °C / Inert atmosphere 6.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 6 steps
1.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
2.1: sodium carbonate / methanol / 0.5 h / 25 °C
3.1: toluene / 5 h / Reflux
4.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
5.2: 4 h / 0 - 20 °C / Inert atmosphere
6.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

: 155855-53-1
(3aR,4S,6R,6aS)-6-(benzylamino)-2,2-dimethyltetrahydro-3ah-cyclopenta-[d][1,3]-dioxol-4-ol

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 4 h / 0 - 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

: 10257-32-6
D-ribose

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: hydrogenchloride / acetone / 22 h / 25 °C 2.1: pyridine / 4 h / -10 - -5 °C 3.1: lithium bromide / butanone / 22 h / 80 °C 4.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 5.1: sodium carbonate / methanol / 0.5 h / 25 °C 6.1: toluene / 5 h / Reflux 7.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 8.2: 4 h / 0 - 20 °C / Inert atmosphere 9.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme
Multi-step reaction with 9 steps 1.1: Dowex WX8 / 72 h / 25 °C 2.1: pyridine / 4 h / -10 - -5 °C 3.1: lithium bromide / butanone / 22 h / 80 °C 4.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 5.1: sodium carbonate / methanol / 0.5 h / 25 °C 6.1: toluene / 5 h / Reflux 7.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 8.2: 4 h / 0 - 20 °C / Inert atmosphere 9.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 9 steps
1.1: hydrogenchloride / acetone / 22 h / 25 °C
2.1: pyridine / 4 h / -10 - -5 °C
3.1: lithium bromide / butanone / 22 h / 80 °C
4.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
5.1: sodium carbonate / methanol / 0.5 h / 25 °C
6.1: toluene / 5 h / Reflux
7.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
8.2: 4 h / 0 - 20 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

Multi-step reaction with 9 steps
1.1: Dowex WX8 / 72 h / 25 °C
2.1: pyridine / 4 h / -10 - -5 °C
3.1: lithium bromide / butanone / 22 h / 80 °C
4.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
5.1: sodium carbonate / methanol / 0.5 h / 25 °C
6.1: toluene / 5 h / Reflux
7.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
8.2: 4 h / 0 - 20 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme

: (3aS,4R,6S,6aR)-N-benzyl-6-(2-(benzyloxy)ethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine fumarate salt

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; ethyl acetate / 1 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

: 1416158-40-1
tert-butyl [[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate L-(+)-tartaric acid salt

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / water; dichloromethane / 20 - 25 °C / pH 10 - 10.5 2: lithium borohydride / dichloromethane / 24 h / 20 - 25 °C / pH 10 - 10.5 / Inert atmosphere View Scheme

: C15H19NO3

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ammonium formate; palladium 10% on activated carbon / methanol / 1.5 h / Reflux 2.1: potassium carbonate / water / 5.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C 3.2: 6.33 h / -20 - 20 °C 4.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C 5.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C View Scheme
Multi-step reaction with 3 steps 1: zinc; acetic acid / tetrahydrofuran / 24 h / 5 - 25 °C 2: Nafion-H / toluene / 5 h / Reflux 3: palladium on activated charcoal; hydrogen / ethanol / 12 h / 50 - 60 °C / 750.08 Torr / Autoclave; Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1.1: ammonium formate; palladium 10% on activated carbon / methanol / 1.5 h / Reflux
2.1: potassium carbonate / water / 5.5 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C
3.2: 6.33 h / -20 - 20 °C
4.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C
5.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C
View Scheme

Multi-step reaction with 3 steps
1: zinc; acetic acid / tetrahydrofuran / 24 h / 5 - 25 °C
2: Nafion-H / toluene / 5 h / Reflux
3: palladium on activated charcoal; hydrogen / ethanol / 12 h / 50 - 60 °C / 750.08 Torr / Autoclave; Inert atmosphere
View Scheme

: 145783-15-9
4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 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

Conditions

Conditions	Yield
Stage #1: 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine; [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol In water; N,N-dimethyl-formamide for 0.333333h; Stage #2: With triethylamine at 20℃; Reflux;	95%
With N-ethyl-N,N-diisopropylamine at 120 - 125℃; for 10h; Temperature; Inert atmosphere;	93.5%
With sodium hydrogencarbonate In water at 100℃; for 20h; Reagent/catalyst; Temperature;	88.3%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 145783-14-8
4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine

: 1265919-25-2
2-[((3aR,4S,6R,6aS)-6-{[5-nitro-6-chloro-2-(propylthio)-4-pyrimidinyl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 10 - 20℃; for 2h;	93.5%
In tetrahydrofuran at 0 - 10℃; for 2h;	45%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: [3aR-(3aα, 4α,6α,6aα)]-[6-azido-2,2-dimethyl-tetrahydro-4H-cyclopenta-1,3-dioxane-4-oxy]ethanol

Conditions

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In acetonitrile at 0 - 20℃; for 3h; Inert atmosphere;	92.6%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 384-98-5
2,4,6-trimethylbenzene-1-sulfonyl fluoride

: N-((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-2,4,6-trimethylbenzenesulfonamide

Conditions

Conditions	Yield
With 1,1,3,3-Tetramethyldisiloxane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃; for 24h; Sealed tube;	92%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 91322-00-8
5-amino-2,4,6-trichloropyrimidine

: 2-(((3aR,4S,6R,6aS)-6-((5-amino-2,6-dichloropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Conditions

Conditions	Yield
With triethylamine at 110℃; Sealed tube;	83%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 1444301-60-3
(1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

Conditions

Conditions	Yield
Stage #1: [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol With hydrogenchloride In methanol; water at 20℃; for 24h; Stage #2: With sodium carbonate In isopropyl alcohol at 20℃; for 24h;	80%
With hydrogenchloride In methanol; water at 10℃; for 11h;	4.0 g

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: C7H9Cl2N3OS

: C17H27ClN4O5S

Conditions

Conditions	Yield
With triethylamine In pentan-1-ol at 115℃; for 10h;	78.75%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: C7H9N5OS

: C17H26N6O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 35℃; for 8h;	75.05%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 4359-87-9
2,4,6-trichloro-5-nitropyrimidine

: 2-(((3aR,4S,6R,6aS)-6-((2,6-dichloro-5-nitropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20℃; for 4h;	59%

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 144-62-7
oxalic acid

: 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

Conditions

Conditions	Yield
In ethanol; water at 65℃;

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 2743-38-6
O,O'-dibenzoyl-L-tartaric acid

: bis[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-aminium] 2,3-bis(benzoyloxy)succinate

Conditions

Conditions	Yield
In ethanol at 10 - 50℃; for 4h;

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate 2: isopentyl nitrite / acetonitrile View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water / 20 h / 100 °C 2: sodium nitrite / water; acetic acid / 2 h / 0 °C View Scheme

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4: hydrogenchloride; water / methanol / 1 h View Scheme
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 2.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 3.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 4.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 4.2: pH > 8 View Scheme
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 2.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 3.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 4.1: potassium carbonate / acetone / 24 h / 25 - 60 °C 5.1: hydrogenchloride; water / methanol / 5.5 h / 20 - 55 °C 5.2: 25 - 30 °C / pH 10 View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: C30H38F2N6O5S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: C29H36F2N6O6S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: C31H40F2N6O6S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C 5.1: iodine / methanol / 4 h / 60 °C View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C 5.1: iodine / methanol / 4 h / 60 °C View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 274693-26-4
[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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h View Scheme
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 2: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 3: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 4: iodine / acetone / 2 h / 25 - 60 °C View Scheme
Multi-step reaction with 3 steps 1: potassium tert-butylate 2: isopentyl nitrite / acetonitrile 3: N-ethyl-N,N-diisopropylamine View Scheme

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 2.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 4.1: triethylamine / acetonitrile / 0.5 h / 20 °C 4.2: 2 h / 20 °C 5.1: iodine / methanol / 4 h / 60 °C View Scheme

Ticagrelor Intermediate1 Specification

The Ticagrelor Intermediate1, with CAS registry number 274693-55-9, has the systematic name of 2-{[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy}ethanol; 1-Acetyladamantane Intermediate;2-(6-Amino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yloxy)-ethanol;. Besides this, it is also called 1-Acetyladamantane Intermediate. And the chemical formula of this chemical is C₁₀H₁₉NO₄.

Physical properties of Ticagrelor Intermediate1: (1)ACD/LogP: -1.48; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 5; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 73.94 Å²; (7)Index of Refraction: 1.52; (8)Molar Refractivity: 54.561 cm³; (9)Molar Volume: 179.494 cm³; (10)Polarizability: 21.63×10^-24cm³; (11)Surface Tension: 45.976 dyne/cm; (12)Density: 1.21 g/cm³; (13)Flash Point: 158.304 °C; (14)Enthalpy of Vaporization: 67.36 kJ/mol; (15)Boiling Point: 338.144 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O1[C@H]2[C@H](N)C[C@H](OCCO)[C@H]2OC1(C)C
(2)InChI: InChI=1/C10H19NO4/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12/h6-9,12H,3-5,11H2,1-2H3/t6-,7+,8+,9-/m1/s1
(3)InChIKey: WNYYMPICYAOQAE-RYPBNFRJBV
(4)Std. InChI: InChI=1S/C10H19NO4/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12/h6-9,12H,3-5,11H2,1-2H3/t6-,7+,8+,9-/m1/s1
(5)Std. InChIKey: WNYYMPICYAOQAE-RYPBNFRJSA-N

Product Name

1-Acetyladamantane Intermediate

Synthetic route

Ticagrelor Intermediate1 Specification

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