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41274-09-3

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41274-09-3 Usage

Uses

Different sources of media describe the Uses of 41274-09-3 differently. You can refer to the following data:
1. A chiral synthon for general asymmetric synthesis. An intermediate for the synthesis of chiral aryloxypropanolamines, which make up the majority of known potent beta-adrenergic blockers
2. A chiral synthon for general asymmetric synthesis. An intermediate for the synthesis of chiral aryloxypropanolamines, which make up the majority of known potent beta-adrenergic blockers.

Check Digit Verification of cas no

The CAS Registry Mumber 41274-09-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,2,7 and 4 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 41274-09:
(7*4)+(6*1)+(5*2)+(4*7)+(3*4)+(2*0)+(1*9)=93
93 % 10 = 3
So 41274-09-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O5S/c1-8-2-4-10(5-3-8)16(13,14)15-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3/t9-/m1/s1

41274-09-3 Well-known Company Product Price

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  • Aldrich

  • (G2410)  (R)-Glycerol1-(p-toluenesulfonate)  95% (TLC)

  • 41274-09-3

  • G2410-1G

  • 3,714.75CNY

  • Detail

41274-09-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-1-Tosyloxy-2,3-propanediol

1.2 Other means of identification

Product number -
Other names [(2R)-2,3-dihydroxypropyl] 4-methylbenzenesulfonate

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:41274-09-3 SDS

41274-09-3Synthetic route

(R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate
23788-74-1

(R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
With hydrogenchloride In acetone Heating;98%
With hydrogenchloride In methanol at 20℃; for 0.5h;98%
With Dowex 50X8 H(+) form In methanol at 60℃; for 7h;96%
(R)-(-)-3-tosyloxy-2-benzyloxy-1-propanol
119870-20-1

(R)-(-)-3-tosyloxy-2-benzyloxy-1-propanol

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol98%
((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate
1638138-12-1

((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 24h;85%
(R)-(+)-3-tosyloxypropane-1,2-diol dipropionate
141656-30-6

(R)-(+)-3-tosyloxypropane-1,2-diol dipropionate

A

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

B

(S)-1-tosyloxy-2,3-propanediol
50765-70-3

(S)-1-tosyloxy-2,3-propanediol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 60℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
allyl tosylate
4873-09-0

allyl tosylate

A

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

B

(S)-1-tosyloxy-2,3-propanediol
50765-70-3

(S)-1-tosyloxy-2,3-propanediol

Conditions
ConditionsYield
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); 1,4-bis(dihydroquinidinyl)anthraquinone In water; tert-butyl alcohol at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(R)-3--1.2-isopropylidenedioxy-propane

(R)-3--1.2-isopropylidenedioxy-propane

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
With hydrogenchloride
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(+-)-erythro-4-<4-nitro-benzoylamino>-pentan-2-ol

(+-)-erythro-4-<4-nitro-benzoylamino>-pentan-2-ol

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / pyridine / 16 h / 0 - 28 °C
2: 95 percent / 1N HCl / acetone / 0.5 h / Heating
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2.4-dioxy-6-methoxy-benzophenone

2.4-dioxy-6-methoxy-benzophenone

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 5 h / 20 °C
2: 3.166 g / TFA / H2O / 0.25 h / 20 °C
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1-propyloxy-ethanol-(2)

1-propyloxy-ethanol-(2)

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / Ambient temperature
2: 1 M HCl / acetone / 90 - 95 °C
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

l(+)-alanine

l(+)-alanine

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / pyridine
2: 98 percent / HCl / acetone / Heating
View Scheme
(R)-1-O-Acetyl-2-O-benzyl-3-tosylglycerol
128223-59-6

(R)-1-O-Acetyl-2-O-benzyl-3-tosylglycerol

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / 25percent NH4OH / methanol / 15 h / Ambient temperature
2: 98 percent / H2 / 5percent Pd/C / ethanol
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / pyridine / 15 h / Ambient temperature
2: 96 percent / 25percent NH4OH / methanol / 15 h / Ambient temperature
3: 98 percent / H2 / 5percent Pd/C / ethanol
View Scheme
Multi-step reaction with 2 steps
1: 2) NaOH / 1) Py., 2) EtOH, 0 deg C
2: 98 percent / H2 / 5percent Pd/C / ethanol
View Scheme
Multi-step reaction with 2 steps
1: pyridine / acetone / 0 °C
2: hydrogenchloride / methanol / 6 h / Reflux
View Scheme
(S) glycerol-1, 2-acetonide

(S) glycerol-1, 2-acetonide

2,2-dimethylvaleroyl chloride
15721-22-9

2,2-dimethylvaleroyl chloride

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
In pyridine; dichloromethane; acetone
(S) glycerol-1,2-acetonide

(S) glycerol-1,2-acetonide

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Conditions
ConditionsYield
With hydrogenchloride In pyridine; dichloromethane; acetone
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-4-tosyloxymethyl-1,3,2-dioxathiolan-2-oxide

(R)-4-tosyloxymethyl-1,3,2-dioxathiolan-2-oxide

Conditions
ConditionsYield
With thionyl chloride; triethylamine In dichloromethane at 0℃; for 0.166667h;93%
α-naphthol
90-15-3

α-naphthol

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-3-(1-naphthyloxy)-1,2-propanediol
61248-78-0

(R)-3-(1-naphthyloxy)-1,2-propanediol

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 80℃; for 16h;91%
pivaloyl imidazole
4195-19-1

pivaloyl imidazole

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(2R)-3-p-toluenesulphonyloxy-1-trimethylacetoxy-2-propanol
141110-71-6

(2R)-3-p-toluenesulphonyloxy-1-trimethylacetoxy-2-propanol

Conditions
ConditionsYield
With triethylamine In dichloromethane for 168h; Ambient temperature;88%
With triethylamine In methanol; dichloromethane; chloroform48.3 g (146 mmol, 88%)
With triethylamine In methanol; dichloromethane; chloroform48.3 g (146 mmol, 88%)
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-O-tosyl-2,3-O-methylidene-D-glycerol
67800-64-0

1-O-tosyl-2,3-O-methylidene-D-glycerol

Conditions
ConditionsYield
With hydrogen cation In benzene Heating;87%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

trityl chloride
76-83-5

trityl chloride

(R)-1-tosyloxy-3-(triphenylmethyloxy)-2-propanol
41274-10-6

(R)-1-tosyloxy-3-(triphenylmethyloxy)-2-propanol

Conditions
ConditionsYield
With pyridine at 0℃; for 24h;85%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

Trimethylacetic acid
75-98-9

Trimethylacetic acid

(2R)-3-p-toluenesulphonyloxy-1-trimethylacetoxy-2-propanol
141110-71-6

(2R)-3-p-toluenesulphonyloxy-1-trimethylacetoxy-2-propanol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;78%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

1-palmitoyl-3-(p-toluenesulfonyl)-sn-glycerol
57984-42-6

1-palmitoyl-3-(p-toluenesulfonyl)-sn-glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;72%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(S)-1,2-Propanediol
4254-15-3

(S)-1,2-Propanediol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h;72%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

4-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-4-oxobutanal
144024-32-8

4-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-4-oxobutanal

A

(R)-(+)-2-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-<(4-methylphenyl)sulfonyloxy>-1-propanol
144024-35-1

(R)-(+)-2-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-<(4-methylphenyl)sulfonyloxy>-1-propanol

B

(R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol
144024-34-0

(R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 3h; Heating;A 5.5%
B 71%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(-)-(2S)-3-azidopropane-1,2-diol
85820-84-4

(-)-(2S)-3-azidopropane-1,2-diol

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide for 24h; Reflux;70%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

4,4-dimethoxy-1-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-1-butanone
144024-31-7

4,4-dimethoxy-1-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-1-butanone

A

(R)-(+)-2-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-<(4-methylphenyl)sulfonyloxy>-1-propanol
144024-35-1

(R)-(+)-2-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-<(4-methylphenyl)sulfonyloxy>-1-propanol

B

(R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol
144024-34-0

(R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 3h; Heating;A 9%
B 68%
With toluene-4-sulfonic acid In toluene for 4h; Heating;A 11%
B 67%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-3-iodo-1,2-propanediol
40425-15-8

(R)-3-iodo-1,2-propanediol

Conditions
ConditionsYield
With sodium iodide In acetone at 90℃; for 9h;65%
12-(2'-naphthylacetyl)aminododecanoic acid p-nitrophenyl ester
932378-51-3

12-(2'-naphthylacetyl)aminododecanoic acid p-nitrophenyl ester

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-(12'-N-[2''-naphthylacetyl]aminolauroyl)-3-(p-toluenesulfonyl)-sn-glycerol
932378-50-2

1-(12'-N-[2''-naphthylacetyl]aminolauroyl)-3-(p-toluenesulfonyl)-sn-glycerol

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 96h;58%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

A

((2S,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

((2S,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

B

((2R,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

((2R,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 48h; Reflux; Dean-Stark; Inert atmosphere;A 55%
B 30%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol
605680-00-0

1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol

Conditions
ConditionsYield
Stage #1: (R)-3-tosyloxy-1,2-propanediol; 1-hexadecylcarboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
Stage #2: 3,4-dihydro-2H-pyran With toluene-4-sulfonic acid In dichloromethane at 20℃; Further stages;
52%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

stearic acid
57-11-4

stearic acid

C26H50O5

C26H50O5

Conditions
ConditionsYield
Stage #1: (R)-3-tosyloxy-1,2-propanediol; stearic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
Stage #2: 3,4-dihydro-2H-pyran With toluene-4-sulfonic acid In dichloromethane at 20℃; Further stages;
49%
4-(4-chlorophenyl) piperazine
38212-33-8

4-(4-chlorophenyl) piperazine

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h; Heating;48%
4-phenyl-1-piperazine
92-54-6

4-phenyl-1-piperazine

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

dextrodropropizine

dextrodropropizine

Conditions
ConditionsYield
In toluene for 18h; Heating;44%
1-(4-methoxyphenyl)piperazine
38212-30-5

1-(4-methoxyphenyl)piperazine

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-3-[4-(4-Methoxy-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(4-Methoxy-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h; Heating;40%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

100

100

(R)-3-[4-(2-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(2-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h;38%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

1-(4-Fluorophenyl)piperazine
2252-63-3

1-(4-Fluorophenyl)piperazine

(R)-3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h; Heating;35%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

N-(m-chlorophenyl)piperazine
6640-24-0

N-(m-chlorophenyl)piperazine

(R)-3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h; Heating;30%
1-(2-Methoxyphenyl)piperazine
35386-24-4

1-(2-Methoxyphenyl)piperazine

(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

(R)-3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propane-1,2-diol

(R)-3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propane-1,2-diol

Conditions
ConditionsYield
In toluene for 18h; Heating;29%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

phenyl isocyanate
103-71-9

phenyl isocyanate

(R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide
96800-34-9

(R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide

Conditions
ConditionsYield
Multistep reaction.;23%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

phenyl isocyanate
103-71-9

phenyl isocyanate

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
Multistep reaction.;22%
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

phenyl isocyanate
103-71-9

phenyl isocyanate

A

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

B

5-(chloromethyl)-3-phenyloxazolidin-2-one

5-(chloromethyl)-3-phenyloxazolidin-2-one

Conditions
ConditionsYield
Multistep reaction;A n/a
B 21%
Multistep reaction;
(R)-3-tosyloxy-1,2-propanediol
41274-09-3

(R)-3-tosyloxy-1,2-propanediol

phenyl isocyanate
103-71-9

phenyl isocyanate

A

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

(5R)-5-chloromethyl-3-phenyl-oxazolidin-2-one

B

(S)-5-Azidomethyl-3-phenyl-oxazolidin-2-one
339301-73-4

(S)-5-Azidomethyl-3-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
Multistep reaction;A n/a
B 15%

41274-09-3Relevant articles and documents

Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol

Manna, Avrajit,Chatterjee, Sandip,Chakraborty, Ipsita,Bhaumik, Tanurima

, (2020/01/08)

Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.

SMALL MOLECULE INHIBITORS OF FIBROSIS

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Paragraph 00472; 00478, (2016/06/28)

Described herein are compounds and compositions for the treatment of a fibrotic disease.

Asymmetric synthesis and effect of absolute stereochemistry of YCZ-2013, a brassinosteroid biosynthesis inhibitor

Oh, Keimei,Yamada, Kazuhiro,Yoshizawa, Yuko

, p. 6915 - 6919 (2014/01/06)

The four stereoisomers of 2RS,4RS-1-[[2-(2,4-dichlorophenyl)-4-(2-(2- propenyloxy)phenoxymethyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole (YCZ-2013), a novel brassinosteroid biosynthesis inhibitor, were prepared. The diastereomers of 2RS,4R-5 and 2RS,4S-5 were prepared by using the corresponding optically pure R and S toluene-4-sulfonic acid 2,3-dihydroxypropyl ester (R-4,S-4). The enatiomerically and diastereomerically pure acetonide (5) was obtained by a method involving diastereoselective crystallisation of the tosylate salt, followed by re-equilibration with the mother liquor and chromatography. The optical purity of four target compounds (YCZ-2013) was confirmed by chiral high-performance liquid chromatography (HPLC) and NMR. The effects of these stereoisomers on Arabidopsis stem elongation indicated that the cis isomers of 2S,4R-YCZ-2013 and 2R,4S-YCZ-2013 exhibited potent inhibitory activity with IC50 values of approximately 24 ± 3 and 24 ± 2 nM, respectively. The IC50 values of the trans isomers of 2S,4S-YCZ-2013 and 2R,4R-YCZ-2013 are approximately 1510 ± 50 and 3900 ± 332 nM, respectively. Co-application of brassinolide (10 nM), the most potent BR, and GA3 (1 μM) to Arabidopsis seedlings grown in the dark with 2R,4S-YCZ-2013 and 2S,4R-YCZ-2013 revealed that brassinolide recovered the induced dwarfism of Arabidopsis seedlings, whereas GA3 showed no effect.

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