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164162-36-1

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164162-36-1 Usage

Description

2-(tert-butyldiMethylsilyl)oxyl alcohol trifluorin methanesulfonate is a chemical compound that serves as an organic synthesis intermediate and pharmaceutical intermediate. It is primarily utilized in laboratory research and development processes, as well as in chemical production processes.

Uses

Used in Organic Synthesis:
2-(tert-butyldiMethylsilyl)oxyl alcohol trifluorin methanesulfonate is used as an organic synthesis intermediate for facilitating various chemical reactions and the formation of new compounds. Its unique structure allows it to act as a versatile building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(tert-butyldiMethylsilyl)oxyl alcohol trifluorin methanesulfonate is used as a pharmaceutical intermediate. It plays a crucial role in the development of new drugs and the improvement of existing ones, contributing to the advancement of medicine and healthcare.
Used in Laboratory Research and Development:
2-(tert-butyldiMethylsilyl)oxyl alcohol trifluorin methanesulfonate is employed in laboratory research and development processes to explore its potential applications and properties. This helps scientists and researchers to better understand its behavior and reactivity, leading to the discovery of new uses and applications.
Used in Chemical Production Process:
In the chemical production process, 2-(tert-butyldiMethylsilyl)oxyl alcohol trifluorin methanesulfonate is utilized to manufacture various chemical products. Its presence in the production process ensures the synthesis of high-quality products with desired properties, contributing to the efficiency and effectiveness of the overall process.

Synthesis

The reaction was carried out under a nitrogen atmosphere. TBS- ethylene glycol prepared as per step 1 (85.10g, 0.48 mol) and 2, 6-Lutidine (84.28ml, 0.72 mol) were stirred in n-heptane (425ml) to give a clear solution which was then cooled to -15 to - 25°C. Trifluoromethanesulfonic anhydride (Tf2O) (99.74 ml, 0.590 mol) was added drop-wise over a period of 45 minutes to the n-heptane solution (white precipitate starts to form immediately) while maintaining the reaction at -15 to -25°C. The reaction mixture was kept at temperature between -15 to -25°C for 2 hours. The precipitate generated was filtered off. The filtrate was then evaporated up to ~2 volumes with respect to TBS-ethyiene glycol (~200 ml).

Check Digit Verification of cas no

The CAS Registry Mumber 164162-36-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,4,1,6 and 2 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 164162-36:
(8*1)+(7*6)+(6*4)+(5*1)+(4*6)+(3*2)+(2*3)+(1*6)=121
121 % 10 = 1
So 164162-36-1 is a valid CAS Registry Number.

164162-36-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

1.2 Other means of identification

Product number -
Other names 2-[tert-butyl(dimethyl)silyl]oxyethyl trifluoromethanesulfonate

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:164162-36-1 SDS

164162-36-1Synthetic route

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-(tert-butyldimethylsilyloxy)ethanol
102229-10-7

2-(tert-butyldimethylsilyloxy)ethanol

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at -28℃; for 0.5h;98.4%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;78.6%
With 2,6-dimethylpyridine In dichloromethane at -78℃; for 0.333333h;
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

2-(tert-butyldimethylsilyloxy)ethanol
102229-10-7

2-(tert-butyldimethylsilyloxy)ethanol

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -18 - 20℃; for 1.33333h; Esterification;
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 12 h / 0 - 30 °C
2: 2,6-dimethylpyridine / n-heptane / 2.75 h / -25 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 0.5 h / -30 °C
2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -28 °C
View Scheme
31-(trimethylsilylether)rapamycin
331810-10-7

31-(trimethylsilylether)rapamycin

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

28-O-TMS-42-O-TBS everolimus

28-O-TMS-42-O-TBS everolimus

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane; toluene at 60℃; for 4h; Time;72.7%
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane; toluene at 60℃; for 4h;72.7%
With 2,6-di-tert-butyl-4-methylpyridine In hexane at 50 - 60℃; for 22h;
sirolimus
53123-88-9

sirolimus

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin
159351-68-5

40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 4.5h; Temperature; Reagent/catalyst;66.4%
With N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 16h; Inert atmosphere;32%
With 2,6-dimethylpyridine In toluene at 55 - 57℃; for 4h; Product distribution / selectivity;
C51H79NO13

C51H79NO13

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

C59H97NO14Si

C59H97NO14Si

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane Product distribution / selectivity;50%
C51H59NO15
1354900-65-4

C51H59NO15

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

C67H95NO17Si2
1551420-98-4

C67H95NO17Si2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 55℃;23%
6-methyl-2(1H)-pyridone
3279-76-3

6-methyl-2(1H)-pyridone

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-pyridin-2-one
874583-88-7

6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-pyridin-2-one

Conditions
ConditionsYield
Stage #1: 6-methyl-2(1H)-pyridone With n-butyllithium; sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 20℃;
15%
2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

C47(14)C4H79NO13
221688-98-8

C47(14)C4H79NO13

C55(14)C4H97NO14Si

C55(14)C4H97NO14Si

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane; toluene at 50℃; for 3h; Etherification;
(4R,5S,6S)-3-((3S,5R)-1-Allyloxycarbonyl-5-pyridin-4-ylmethyl-pyrrolidin-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
156442-85-2

(4R,5S,6S)-3-((3S,5R)-1-Allyloxycarbonyl-5-pyridin-4-ylmethyl-pyrrolidin-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-yl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridinium; trifluoro-methanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-yl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridinium; trifluoro-methanesulfonate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 96h;
allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-[(1-methylpyrazol-5-yl)methyl]pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
156442-96-5

allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-[(1-methylpyrazol-5-yl)methyl]pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

5-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-2H-pyrazol-1-ium; trifluoro-methanesulfonate

5-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-2H-pyrazol-1-ium; trifluoro-methanesulfonate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 96h;
(4R,5S,6S)-3-[(3S,5R)-1-Allyloxycarbonyl-5-(3-methyl-3H-imidazol-4-ylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
156442-97-6

(4R,5S,6S)-3-[(3S,5R)-1-Allyloxycarbonyl-5-(3-methyl-3H-imidazol-4-ylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-3H-imidazol-1-ium; trifluoro-methanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-3H-imidazol-1-ium; trifluoro-methanesulfonate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 96h;
(4R,5S,6S)-3-[(3S,5R)-1-Allyloxycarbonyl-5-(1-methyl-1H-pyrazol-4-ylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
156442-89-6

(4R,5S,6S)-3-[(3S,5R)-1-Allyloxycarbonyl-5-(1-methyl-1H-pyrazol-4-ylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-2H-pyrazol-1-ium; trifluoro-methanesulfonate

4-{1-allyloxycarbonyl-4-[2-allyloxycarbonyl-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-2H-pyrazol-1-ium; trifluoro-methanesulfonate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 96h;
39-O-desmethoxy-rapamycin
821792-15-8

39-O-desmethoxy-rapamycin

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

C58H95NO13Si

C58H95NO13Si

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine In dichloromethane at 20℃; for 72h;
4,6-dichloro-N-(6-iodopyridin-3-yl)pyrimidine-5-carboxamide

4,6-dichloro-N-(6-iodopyridin-3-yl)pyrimidine-5-carboxamide

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate
164162-36-1

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate

N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4,6-dichloro-N-(6-iodopyridin-3-yl)pyrimidine-5-carboxamide

N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4,6-dichloro-N-(6-iodopyridin-3-yl)pyrimidine-5-carboxamide

Conditions
ConditionsYield
Stage #1: 4,6-dichloro-N-(6-iodopyridin-3-yl)pyrimidine-5-carboxamide With sodium hexamethyldisilazane In tetrahydrofuran at -23 - -20℃; for 0.75h;
Stage #2: 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate In tetrahydrofuran at -20 - 20℃; for 2.25h;

164162-36-1Relevant articles and documents

RAPAMYCIN ANALOGS AND USES THEREOF

-

Paragraph 0349-00350, (2020/01/08)

The present invention provides compounds, compositions thereof, and methods of using the same.

Preparation method of everolimus intermediate

-

, (2017/12/30)

The invention discloses a preparation method of an everolimus intermediate. The preparation method comprises the following steps: reacting ethylene glycol and tert-butyldimethylsilyl chloride in inert solvents such as dichloromethane at the temperature of 35 DEG C below zero to 25 DEG C below zero in the presence of organic base to obtain 2-(tert-dimethylsiloxy)ethyl alcohol; reacting the 2-(tert-dimethylsiloxy)ethyl alcohol and trifluoromethanesulfonic anhydride in the presence of the organic base to obtain trifluoromethanesulfonic acid 2-(tert-dimethylsiloxy)ethyl ester. According to the method disclosed by the invention, the generation of a disubstituted by-product can be greatly reduced, and further a monosubstituted product 2-(tert-dimethylsiloxy) ethyl alcohol with relatively-high purity and yield is obtained.

PYRIDINE DERIVATIVES AS DGAT-1 INHIBITORS

-

Page/Page column 20; 37-38, (2014/09/29)

Described herein are compounds of formula (I): The compounds of formula (I) act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.

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