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52509-14-5 Usage

Chemical Properties

white to light brown granular powder

Uses

Different sources of media describe the Uses of 52509-14-5 differently. You can refer to the following data:
1. (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium Bromide is used as a reactant in the synthesis of ketolides methyloxoerythromycins with antibacterial activity as highly potent against macrolide-resistant and susceptible respiratory pathogens.
2. Reactant for:Preparation of a ratiometric fluorescent probe for specific detection of cysteine over homocysteine and glutathioneMicrowave-assisted synthesis of KN-93 as inhibitor of calmodulin kinase IIPreparation of fluorinated spirobenzofuran piperidines as s1 receptor ligandsSynthesis and antitumor agentsRegio-selective preparation of indole derivatives via rhodium-catalyzed domino hydroformylation/indolization

Purification Methods

Wash the crystals with Et2O, dry them in a vacuum and recrystallise them from CH2Cl2/dry Et2O to give prisms m 172-174o, which is raised to 191.5-193o on drying at 56o/0.5mm. [Cresp et al. J Chem Soc, Perkin Trans 1 37 1974.]

Check Digit Verification of cas no

The CAS Registry Mumber 52509-14-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,5,0 and 9 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 52509-14:
(7*5)+(6*2)+(5*5)+(4*0)+(3*9)+(2*1)+(1*4)=105
105 % 10 = 5
So 52509-14-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H22O2P.BrH/c1-4-10-19(11-5-1)25(18-22-23-16-17-24-22,20-12-6-2-7-13-20)21-14-8-3-9-15-21;/h1-15,22H,16-18H2;1H/q+1;/p-1

52509-14-5 Well-known Company Product Price

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  • TCI America

  • (D2164)  (1,3-Dioxolan-2-yl)methyltriphenylphosphonium Bromide  >97.0%(T)

  • 52509-14-5

  • 5g

  • 440.00CNY

  • Detail
  • TCI America

  • (D2164)  (1,3-Dioxolan-2-yl)methyltriphenylphosphonium Bromide  >97.0%(T)

  • 52509-14-5

  • 25g

  • 1,280.00CNY

  • Detail
  • Alfa Aesar

  • (A18882)  (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide, 98%   

  • 52509-14-5

  • 10g

  • 577.0CNY

  • Detail
  • Alfa Aesar

  • (A18882)  (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide, 98%   

  • 52509-14-5

  • 50g

  • 2111.0CNY

  • Detail
  • Alfa Aesar

  • (A18882)  (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide, 98%   

  • 52509-14-5

  • 250g

  • 9056.0CNY

  • Detail
  • Aldrich

  • (223859)  (1,3-Dioxolan-2-ylmethyl)triphenylphosphoniumbromide  98%

  • 52509-14-5

  • 223859-5G

  • 1,021.41CNY

  • Detail

52509-14-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

1.2 Other means of identification

Product number -
Other names 1,3-dioxolan-2-ylmethyl(triphenyl)phosphanium,bromide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52509-14-5 SDS

52509-14-5Synthetic route

2-bromomethyl-1,3-dioxolane
4360-63-8

2-bromomethyl-1,3-dioxolane

triphenylphosphine
603-35-0

triphenylphosphine

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In isopropyl alcohol at 60 - 65℃; for 3h; Inert atmosphere; Green chemistry;99.1%
In toluene for 24h; Heating / reflux;54%
at 120℃; for 24h;
2-bromomethyl-1,3-dioxolane
4360-63-8

2-bromomethyl-1,3-dioxolane

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 48h; Reflux;33%
4,15-diformyl[2.2]paracyclophane
288156-11-6

4,15-diformyl[2.2]paracyclophane

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane

4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane

Conditions
ConditionsYield
Stage #1: 4,15-diformyl[2.2]paracyclophane; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran at 2℃; for 16h;
100%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane

4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane

(2E,4E,6E)-7-[12-((1E,3E,5E)-7-Oxo-hepta-1,3,5-trienyl)-tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaen-5-yl]-hepta-2,4,6-trienal

(2E,4E,6E)-7-[12-((1E,3E,5E)-7-Oxo-hepta-1,3,5-trienyl)-tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaen-5-yl]-hepta-2,4,6-trienal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran at 2℃; for 16h;
100%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

(E)-3-(4-iodophenyl)acrylaldehyde

(E)-3-(4-iodophenyl)acrylaldehyde

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; p-(iodophenyl)carboxaldehyde With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 25℃; for 14h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 25℃; for 6h;
100%
With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;78.7%
mesytaldehyde
487-68-3

mesytaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

2-(2,4,6-trimethylstyryl)-1,3-dioxolane

2-(2,4,6-trimethylstyryl)-1,3-dioxolane

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: mesytaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
100%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

5-((allyloxy)methyl)furan-2-carbaldehyde
113675-57-3

5-((allyloxy)methyl)furan-2-carbaldehyde

C11H12O3

C11H12O3

Conditions
ConditionsYield
With sodium methylate In methanol; N,N-dimethyl-formamide at 70℃; for 48h; Wittig Olefination; Inert atmosphere;99%
(E)-3-(methylthio)cinnamaldehyde
1421970-17-3

(E)-3-(methylthio)cinnamaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(2E,4E)-5-(3-(methylthio)phenyl)penta-2,4-dienal
1421970-16-2

(2E,4E)-5-(3-(methylthio)phenyl)penta-2,4-dienal

Conditions
ConditionsYield
Stage #1: (E)-3-(methylthio)cinnamaldehyde; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium methylate In methanol at 25℃; Wittig Olefination; Inert atmosphere;
Stage #2: With iodine In methanol; acetone for 12h; Inert atmosphere; Reflux;
96.2%
C17H26O
860032-97-9

C17H26O

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C19H28O
1254522-05-8

C19H28O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C17H26O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water
96%
quinoline-4-carboxaldehyde
4363-93-3

quinoline-4-carboxaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-quinoline
172678-77-2

4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-quinoline

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -35 - 10℃; for 4h;95%
With lithium methanolate In methanol; N,N-dimethyl-formamide at 70 - 80℃; for 4h;
With potassium tert-butylate In tetrahydrofuran
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-ethyl-6-(2-oxoethyl)piperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-ethyl-6-(2-oxoethyl)piperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-6-[3-(1,3-dioxolan-2-yl)prop-2-enyl]-5-ethylpiperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-6-[3-(1,3-dioxolan-2-yl)prop-2-enyl]-5-ethylpiperidine-1,2-dicarboxylate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran Condensation; Wittig reaction;95%
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 0.5h;
Stage #2: 1-benzyl, 2-methyl (2RS,5RS,6RS)-5-ethyl-6-(2-oxoethyl)piperidine-1,2-dicarboxylate In tetrahydrofuran Wittig reaction; Further stages.;
95%
C21H30O
1254522-33-2

C21H30O

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C23H32O
1254522-09-2

C23H32O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C21H30O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water
95%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

7-diethylaminocoumarine-3-aldehyde
57597-64-5

7-diethylaminocoumarine-3-aldehyde

(E)-3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)acrylaldehyde
1403769-30-1

(E)-3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)acrylaldehyde

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 7-diethylaminocoumarine-3-aldehyde In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydroxide In dichloromethane at 20℃; for 3h;
Stage #3: With hydrogenchloride In dichloromethane at 20℃; for 0.2h;
95%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

5-(N,N-dibutylamino)-thiophene-2-carbaldehyde
159874-90-5

5-(N,N-dibutylamino)-thiophene-2-carbaldehyde

(E)-3-(5-(dibutylamino)thiophene-2-yl)acrylaldehyde

(E)-3-(5-(dibutylamino)thiophene-2-yl)acrylaldehyde

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 0.5h; Wittig Olefination; Cooling with ice;
Stage #2: 5-(N,N-dibutylamino)-thiophene-2-carbaldehyde In tetrahydrofuran at 20℃;
Stage #3: With oxalic acid In tetrahydrofuran; water for 24h;
94%
C19H28O
1254522-05-8

C19H28O

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C21H30O
1254522-33-2

C21H30O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C19H28O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water
93%
(E)-3-(5-(dimethylamino)thiophen-2-yl)acrylaldehyde

(E)-3-(5-(dimethylamino)thiophen-2-yl)acrylaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(2E,4E)-5-(5-(dimethylamino)thiophen-2-yl)penta-2,4-dienal

(2E,4E)-5-(5-(dimethylamino)thiophen-2-yl)penta-2,4-dienal

Conditions
ConditionsYield
With 18-crown-6 ether; sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 12h;92.9%
3-(4-dimethylamino-phenyl)-propenal
20432-35-3, 6203-18-5

3-(4-dimethylamino-phenyl)-propenal

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal
20432-36-4

s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal

Conditions
ConditionsYield
Stage #1: 3-(4-dimethylamino-phenyl)-propenal; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; Wittig reaction;
Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; for 2h;
92%
With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; for 12h;58.6%
Stage #1: 3-(4-dimethylamino-phenyl)-propenal; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; for 2h; Wittig Rearrangement; Cooling with ice;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;
Stage #3: With potassium carbonate In tetrahydrofuran; water at 20℃;
55%
Stage #1: 3-(4-dimethylamino-phenyl)-propenal; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With 18-crown-6 ether; sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 12h; Wittig Olefination;
Stage #2: With hydrogenchloride at 20℃; for 0.5h;
39%
Stage #1: 3-(4-dimethylamino-phenyl)-propenal; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With 18-crown-6 ether; sodium hydride In tetrahydrofuran
Stage #2: With hydrogenchloride In tetrahydrofuran
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane

4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane

4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane

4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran at 2℃; for 16h;
92%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(2-[(N-benzylprolyl)amino]benzophenone)
95019-19-5

(2-[(N-benzylprolyl)amino]benzophenone)

(2E,8E,10E)-dodeca-2,8,10-trienal
864818-23-5

(2E,8E,10E)-dodeca-2,8,10-trienal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate at 0℃;
Stage #2: (2-[(N-benzylprolyl)amino]benzophenone) for 1h;
Stage #3: With oxalic acid at 20℃; Further stages.;
91%
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (2-[(N-benzylprolyl)amino]benzophenone) In tetrahydrofuran at 0℃; for 3h;
64%
(1S,2R)-1-(3,4-dichlorophenyl)-2-formyl-cyclopropanecarboxylic acid (4-fluorobenzyl)methylamide
846060-69-3

(1S,2R)-1-(3,4-dichlorophenyl)-2-formyl-cyclopropanecarboxylic acid (4-fluorobenzyl)methylamide

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 2h;91%
C15H24O
1242261-02-4

C15H24O

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C17H26O
860032-97-9

C17H26O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C15H24O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water
91%
2-methylthiobenzaldehyde

2-methylthiobenzaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(E)-2-methylthiocinnamaldehyde
1356939-86-0

(E)-2-methylthiocinnamaldehyde

Conditions
ConditionsYield
Stage #1: 2-methylthiobenzaldehyde; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium hydride; 18-crown-6 ether In tetrahydrofuran at 20℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃;
90.4%
6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol at 10 - 20℃; for 4h; Inert atmosphere; Green chemistry;90.1%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-[(tert-butyldimethylsilyl)oxy]-6-(2-oxoethyl)piperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-[(tert-butyldimethylsilyl)oxy]-6-(2-oxoethyl)piperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-[(tert-butyldimethylsilyl)oxy]-6-[3-(1,3-dioxolan-2-yl)prop-2-enyl]piperidine-1,2-dicarboxylate

1-benzyl, 2-methyl (2RS,5RS,6RS)-5-[(tert-butyldimethylsilyl)oxy]-6-[3-(1,3-dioxolan-2-yl)prop-2-enyl]piperidine-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 0.5h;
Stage #2: 1-benzyl, 2-methyl (2RS,5RS,6RS)-5-[(tert-butyldimethylsilyl)oxy]-6-(2-oxoethyl)piperidine-1,2-dicarboxylate In tetrahydrofuran Wittig reaction; Further stages.;
90%
(1RS,2RS,3RS,4RS,6SR)-6-hydroxy-3,4,6-trimethyl-5,8-dioxobicyclo[2.2.2]octane-2-carbaldehyde

(1RS,2RS,3RS,4RS,6SR)-6-hydroxy-3,4,6-trimethyl-5,8-dioxobicyclo[2.2.2]octane-2-carbaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(1RS,3SR,4RS,7RS,8SR)-8-[2-(1,3-dioxolan-2-yl)-vinyl]-3-hydroxy-1,3,7-trimethylbicyclo[2.2.2]octane-2,6-dione

(1RS,3SR,4RS,7RS,8SR)-8-[2-(1,3-dioxolan-2-yl)-vinyl]-3-hydroxy-1,3,7-trimethylbicyclo[2.2.2]octane-2,6-dione

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: (1RS,2RS,3RS,4RS,6SR)-6-hydroxy-3,4,6-trimethyl-5,8-dioxobicyclo[2.2.2]octane-2-carbaldehyde In tetrahydrofuran at 20℃; for 0.333333h; Wittig reaction; Further stages.;
90%
C23H32O
1254522-09-2

C23H32O

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C25H34O
1254522-11-6

C25H34O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C23H32O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water
90%
trans-4-(4-pentylcyclohexyl)-cyclohexane carboxaldehyde

trans-4-(4-pentylcyclohexyl)-cyclohexane carboxaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

C22H38O2

C22H38O2

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -30℃; for 1h;
Stage #2: trans-4-(4-pentylcyclohexyl)-cyclohexane carboxaldehyde In tetrahydrofuran at 20℃; for 5h;
90%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(E)-3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)prop-2-enal
124931-24-4

(E)-3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)prop-2-enal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Sealed tube; Inert atmosphere;
Stage #2: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran at 20℃; for 6h; Sealed tube; Inert atmosphere;
90%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(E)-3-(pyridin-4-yl)acrylaldehyde
32986-66-6

(E)-3-(pyridin-4-yl)acrylaldehyde

Conditions
ConditionsYield
Stage #1: pyridine-4-carbaldehyde; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; Wittig reaction;
Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; for 2h;
89%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4-(1H-pyrazol-1-yl)benzaldehyde
99662-34-7

4-(1H-pyrazol-1-yl)benzaldehyde

(2E)-3-[4-(1H-Pyrazol-1-yl)phenyl]-2-propenal
545424-10-0

(2E)-3-[4-(1H-Pyrazol-1-yl)phenyl]-2-propenal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 4-(1H-pyrazol-1-yl)benzaldehyde With potassium carbonate; Tris(3,6-dioxaheptyl)amine In dichloromethane; water for 20h; Heating / reflux;
Stage #2: With water; hydrogenchloride In tetrahydrofuran at 20℃; for 1h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water at 0℃;
89%
3-formyl-10-methylphenothiazine
4997-36-8

3-formyl-10-methylphenothiazine

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

(E)-3-(10-methyl-10H-phenothiazin-3-yl)acrylaldehyde
1374005-27-2

(E)-3-(10-methyl-10H-phenothiazin-3-yl)acrylaldehyde

Conditions
ConditionsYield
With Tris(3,6-dioxaheptyl)amine; potassium carbonate In dichloromethane for 20h; Reflux;88.6%
Stage #1: 3-formyl-10-methylphenothiazine; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With Tris(3,6-dioxaheptyl)amine; potassium carbonate In dichloromethane for 0.2h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 1h;
80%
Stage #1: 3-formyl-10-methylphenothiazine; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With Tris(3,6-dioxaheptyl)amine; potassium carbonate In dichloromethane for 24h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h;
65%

52509-14-5Relevant articles and documents

COMPOUND ACTING AS ANTIBIOTICS

-

Paragraph 0174; 0176, (2020/12/22)

The present invention provides a novel antibiotic compound represented by the following formula (I), a pharmaceutically acceptable salt thereof, an ester thereof, a prodrug thereof, a solvate thereof, or a deuterated analog thereof, or a stereoisomer thereof. The compound of the present invention exhibits excellent antibacterial activity, especially against Gram bacteria. wherein each group is defined as in the description.

A selective colorimetric and ratiometric fluorescent probe for hydrogen sulfide

Wu, Ming-Yu,Li, Kun,Hou, Ji-Ting,Huang, Zheng,Yu, Xiao-Qi

, p. 8342 - 8347,6 (2012/12/12)

A reaction-based colorimetric and ratiometric fluorescent probe based on an ICT-strategy for selective detection of H2S that exploited the H2S-mediated reduction of nitrocompound to amines was explored. And it displayed high selectivity for H2S over other relevant reactive sulfur, oxygen, nitrogen species and other anions with more than 120 nm blue shift and the change of emission intensity ratio inducted by H2S was over 4750.

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