(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester supplier

Name
(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
EINECS 1592732-453-0
CAS No. 147489-06-3
Article Data21
CAS DataBase
Density 1.184 g/cm³
Solubility
Melting Point 105-116 °C(Solv: hexane (110-54-3))
Formula C₃₂H₃₆FNO₄
Boiling Point 604.559 °C at 760 mmHg
Molecular Weight 517.641
Flash Point 319.426 °C
Transport Information
Appearance white or almost white power
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,3-Dioxane-4-aceticacid,6-[2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-,1,1-dimethylethyl ester, [4R-[4a,6a(E)]]-;(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2,2-Dimethyl-1,3-dioxane-6-heptenoic acid,1,1-dimethylethyl ester;
PSA 57.65000
LogP 7.57350

Synthetic route

: C21H28N2O6S2

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at -10 - 25℃; for 4h;	89.6%

: C15H24N2O6S2

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h;	89.3%

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 154057-57-5
diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With lithium chloride In tetrahydrofuran at 0 - 35℃; for 5.66667h; Reagent/catalyst; Inert atmosphere;	89%
With n-butyllithium In tetrahydrofuran at -80 - -10℃; for 1h; Solvent; Temperature; Inert atmosphere;	71%

: C16H26N2O6S2

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h; Temperature;	88.3%

: 1234331-54-4
2-({[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methyl}sulfonyl)benzo[d]thiazole

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30 - 20℃; Product distribution / selectivity;	86%

: C18H28N2O6S2

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h;	82.5%

: ((2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methyl)triphenylphosphoniumchloride

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 30 - 50℃; for 3h; Large scale;	80.2%

: 153968-97-9
2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline

: 153968-91-3
t-butyl (3R,5S,6E)-3,5-isopropylidenedioxy-7-chlorodimethylsilyl-6-heptenoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 0.5h;	80%

: C31H38O4P(1+)*Cl(1-)

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80 - 85℃; for 1h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	79.2%

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide In dimethyl sulfoxide at 35℃; Large scale; Stage #2: With potassium carbonate In dimethyl sulfoxide at 70℃; for 4h; Solvent; Time; Temperature; Large scale;	72.3%
With potassium carbonate In dimethyl sulfoxide at 70℃; for 3h; Inert atmosphere;	55.8%
With potassium carbonate In dimethyl sulfoxide at 70℃; for 3h; Wittig Reaction;

: C19H15BrFNZn

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0 - 30℃; for 16.5h; Reagent/catalyst; Wittig Olefination;	66.7%

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 146578-99-6
<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide

A: tert-butyl (3R,5S,6Z)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl}-3,5-isopropylidenedioxy-6-heptenoate

B: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran for 3h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 153968-97-9
2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline

: 160375-25-7
t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); dimethylmonochlorosilane; tetrabutyl ammonium fluoride; triethyl phosphite; t-Bu3P*Pt(CH2=CH)SiMe2)2O 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h; Yield given. Multistep reaction;

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 146578-99-6
<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, RT, 30 min, 2.) THF, 3 h; Yield given. Multistep reaction;

: 2-cyclopropyl-4-(4-fluorophenyl)-3-{[(1-methyl-1H-benzo[d]imidazol-2-yl)sulfonyl]methyl}quinoline

: 124752-23-4
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 25 - 35℃; for 3h;

: 5292-43-3
bromoacetic acid tert-butyl ester

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 60 percent / Zn / tetrahydrofuran / 1 h / 80 °C 2: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h 3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 4: p-toluenesulfonic acid / 2 h / Ambient temperature 5: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 6: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 1.) Zn, 2.) HCl aq. / 1.) THF, 1 h, reflux, 2.) 0.5 h 2: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C 3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 4: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 60 percent / Zn / tetrahydrofuran / 1 h / 80 °C
2: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: p-toluenesulfonic acid / 2 h / Ambient temperature
5: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
6: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme

Multi-step reaction with 4 steps
1: 1.) Zn, 2.) HCl aq. / 1.) THF, 1 h, reflux, 2.) 0.5 h
2: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme

: 153968-98-0
(3S)-5-(t-butyldimethylsilyl)-3-hydroxy-4-pentynenitrile

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 60 percent / Zn / tetrahydrofuran / 1 h / 80 °C 2: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h 3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 4: p-toluenesulfonic acid / 2 h / Ambient temperature 5: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 6: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 1.) Zn, 2.) HCl aq. / 1.) THF, 1 h, reflux, 2.) 0.5 h 2: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C 3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 4: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h View Scheme

Yield

: 153969-00-7
t-butyl (3R,5S)-7-(t-butyldimethylsilyl)-3,5-dihydroxy-6-heptynoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 2: p-toluenesulfonic acid / 2 h / Ambient temperature 3: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 4: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 2: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h View Scheme

: 153968-99-1
t-butyl (5S)-7-(t-butyldimethylsilyl)-5-hydroxy-3-oxo-6-heptynoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h 2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 3: p-toluenesulfonic acid / 2 h / Ambient temperature 4: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 5: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C 2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C 3: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h View Scheme

Yield

Multi-step reaction with 5 steps
1: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h
2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
3: p-toluenesulfonic acid / 2 h / Ambient temperature
4: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
5: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme

Multi-step reaction with 3 steps
1: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C
2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
3: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme

: 160375-25-7
t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / 2 h / Ambient temperature 2: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 3: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme

: 153969-01-8
t-butyl (3R,5S)-3,5-syn-isopropylidenedioxy-6-heptynoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature 2: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C View Scheme

: 154057-56-4
3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / toluene / 12 h / Heating 2: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 2 steps 1: isopropyl alcohol; toluene / 4 h / 25 - 50 °C / Industry scale 2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: isopropyl alcohol; toluene / 3 h / 50 °C / Industry scale 2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Industry scale View Scheme
Multi-step reaction with 2 steps 1: isopropyl alcohol; toluene / 50 °C 2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Inert atmosphere; Industry scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 100 - 110 °C 2: n-butyllithium / tetrahydrofuran / 1 h / -80 - -10 °C / Inert atmosphere View Scheme

: 147489-02-9
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-dihydroxy-4,6-isopropylidenedioxyheptanoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 2: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 2 steps 1: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 2: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

: 147489-00-7
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 3: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 4: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 4 steps 1: 98 percent / p-TsOH / 2 h / Ambient temperature 2: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 3: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 4: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

: 147489-01-8
isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 2: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 3: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 3 steps 1: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 2: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 3: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

: 147488-99-1
isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h 2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 5: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 5 steps 1: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h 2: 98 percent / p-TsOH / 2 h / Ambient temperature 3: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 4: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 5: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 5 steps
1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
5: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme

Multi-step reaction with 5 steps
1: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
2: 98 percent / p-TsOH / 2 h / Ambient temperature
3: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
5: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme

: 147488-98-0
isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C 2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h 3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 6: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 6 steps 1: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C 2: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h 3: 98 percent / p-TsOH / 2 h / Ambient temperature 4: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 5: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 6: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C
2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
6: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme

Multi-step reaction with 6 steps
1: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
2: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
3: 98 percent / p-TsOH / 2 h / Ambient temperature
4: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
6: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme

: 121660-11-5
2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / phosphorus tribromide / CH2Cl2; toluene / 3 h / Ambient temperature 2: 100 percent / toluene / 12 h / Heating 3: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h View Scheme
Multi-step reaction with 3 steps 1.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 25 °C / Industry scale 1.2: pH 7 - 8 2.1: isopropyl alcohol; toluene / 4 h / 25 - 50 °C / Industry scale 3.1: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: phosphorus tribromide / dichloromethane / 0 - 25 °C / Industry scale 2: isopropyl alcohol; toluene / 3 h / 50 °C / Industry scale 3: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Industry scale View Scheme

: 1694-31-1
tert-butyl acetoacetate

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 74 percent / NaH, n-BuLi / 20 h / -78 °C 2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C 3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h 4: 98 percent / p-TsOH / 2 h / Ambient temperature 5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 7: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 74 percent / NaH, n-BuLi / 20 h / -78 °C
2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
4: 98 percent / p-TsOH / 2 h / Ambient temperature
5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
7: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme

: 765-43-5
Cyclopropyl methyl ketone

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 0.25 h / 25 °C 1.2: 14 h / 10 - 75 °C / Inert atmosphere 1.3: 0.75 h / 0 - 25 °C / pH 2.5 2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C 2.2: 0.75 h / 0 - 25 °C / pH 6 3.1: toluene / 5 h / 25 °C / Inert atmosphere 3.2: 3 h 3.3: 2 h / 40 °C 4.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 0.25 h / 25 °C 1.2: 14 h / 10 - 75 °C / Inert atmosphere 1.3: 0.75 h / 0 - 25 °C / pH 2.5 2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C 2.2: 0.75 h / 0 - 25 °C / pH 6 3.1: diisobutylaluminium hydride / toluene / 2 h / 0 - 25 °C 3.2: 0.25 h / 10 °C 4.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C 4.2: 1 h / 75 °C 5.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: toluene / 0.25 h / 25 °C
1.2: 14 h / 10 - 75 °C / Inert atmosphere
1.3: 0.75 h / 0 - 25 °C / pH 2.5
2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C
2.2: 0.75 h / 0 - 25 °C / pH 6
3.1: toluene / 5 h / 25 °C / Inert atmosphere
3.2: 3 h
3.3: 2 h / 40 °C
4.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
View Scheme

Multi-step reaction with 5 steps
1.1: toluene / 0.25 h / 25 °C
1.2: 14 h / 10 - 75 °C / Inert atmosphere
1.3: 0.75 h / 0 - 25 °C / pH 2.5
2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C
2.2: 0.75 h / 0 - 25 °C / pH 6
3.1: diisobutylaluminium hydride / toluene / 2 h / 0 - 25 °C
3.2: 0.25 h / 10 °C
4.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C
4.2: 1 h / 75 °C
5.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
View Scheme

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

: (3R,5S,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl>-3,5-dihydroxy-6-heptenoic acid 1,5-lactone

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In methanol; water; acetone Reflux;	99%
With trifluoroacetic acid	74%
With trifluoroacetic acid In dichloromethane for 16h; Ambient temperature;	67%
With trifluoroacetic acid In dichloromethane for 16h; Ambient temperature;	67%
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With hydrogenchloride; water In acetonitrile at 30℃; for 2h; Stage #2: With sodium hydroxide In water; acetonitrile at 35℃; for 2h; Product distribution / selectivity;

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

: 586966-54-3
(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 40℃; for 2h;	95.2%
With hydrogenchloride; water In acetonitrile for 3h; Large scale;	88.4%
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With water; oxalic acid In methanol at 35℃; for 6h; Stage #2: With sodium carbonate In methanol; water at 10 - 30℃; for 2.75h; pH=7;
With hydrogenchloride; water In acetonitrile at 25 - 55℃; pH=2.5;	27 g
With hydrogenchloride In water; acetonitrile at 13℃; for 2h;

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With trifluoroacetic acid In acetonitrile at 30 - 35℃; Stage #2: With caesium carbonate In acetonitrile at 35 - 40℃;	94%
Multi-step reaction with 3 steps 1.1: water; oxalic acid / methanol / 6 h / 35 °C 1.2: 2.75 h / 10 - 30 °C / pH 7 2.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C 2.2: 0.67 h / 25 °C 3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 4 steps 1.1: water; oxalic acid / methanol / 6 h / 35 °C 1.2: 2.75 h / 10 - 30 °C / pH 7 2.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C 2.2: 0.25 h / 0 °C / pH 4 2.3: 0.5 h / 0 °C 3.1: sodium hydroxide / water / 0.75 h / 30 °C 3.2: 0.75 h / 35 °C 4.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / acetonitrile; water / 2 h / 13 °C 2: sodium hydroxide / water / 2 h / 10 °C / Large scale View Scheme

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Chemical Properties

Molecular structure of (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (CAS NO.147489-06-3) is:

Product Name: (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
CAS Registry Number: 147489-06-3
Molecular Formula: C₃₂H₃₆FNO₄
Molecular Weight: 517.64

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Specification

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester , its cas register number is 147489-06-3. It also can be called 1,3-Dioxane-4-aceticacid,6-[(1E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-,1,1-dimethylethyl ester, (4R,6S)- ; (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2,2-Dimethyl-1,3-dioxane-6-heptenoic acid,1,1-dimethylethyl ester .

Product Name

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Synthetic route

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Chemical Properties

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Specification

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