23214-66-6

Basic information

• Product Name: (R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL
• Synonyms: 1-BENZYL-SN-GLYCEROL 3-TOSYLATE;R(-)-3-BENZYLOXY-1,2-PROPANEDIOL 1-(TOLUENE-4-SULFONATE);(R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL;R(-)-1-BENZYLOXY-3-TOSYLOXY-2-PROPANOL;(R)-(-)-3-Benzyloxy-1,2-propanediol 1-(p-toluenesulfonate);3-benzyloxy-1,2-propanediol 1-(toluene-4-sulfonate);(R)-(-)-1-Benzyloxy-3-tosyloxy-2-propanol, 1-Benzyl-sn-glycerol 3-tosylate;(R)-(-)-1-Benzyloxy-3-tosyloxy-2-propanol, 1-Benzyl-sn-glycerol 3-tosylate, (R)-(-)-3-Benzyloxy-1,2-propanediol 1-(p-toluenesulfonate)
• CAS NO: 23214-66-6
• Molecular Formula: C₁₇H₂₀O₅S
• Molecular Weight: 336.4
• Mol File: 23214-66-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 52-55 °C
• Boiling Point: 515.624 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.254 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• PKA: 12.98±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL(23214-66-6)
• EPA Substance Registry System: (R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL(23214-66-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 23214-66-6(Hazardous Substances Data)

Usage

Description

(R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol is an organic compound with a unique structure that features a benzyloxy group at the first carbon, a p-tosyloxy group at the third carbon, and a hydroxyl group at the second carbon. (R)-(-)-1-BENZYLOXY-3-(P-TOSYLOXY)-2-PROPANOL is known for its applications in various chemical reactions and syntheses due to its specific stereochemistry and functional groups.

Uses

(R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol is used as a reagent in enantioselective carbohydrate, terpene, and alkaloid syntheses. Its chiral nature allows for the selective formation of desired enantiomers in these syntheses, which is crucial for the biological activity and pharmaceutical applications of the target molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol is used as a key intermediate in the synthesis of various chiral drugs. Its ability to control the stereochemistry of the final product makes it a valuable tool in the development of new medications with improved efficacy and reduced side effects.
Used in Surfactant Industry:
(R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol is also used in the synthesis of polyhydroxyl surfactants. These surfactants are important in various applications, such as detergents, emulsifiers, and stabilizers, due to their ability to reduce surface tension and form micelles. The chiral nature of (R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol can contribute to the development of more effective and environmentally friendly surfactants.

InChI:InChI=1/C17H20O5S/c1-14-7-9-17(10-8-14)23(19,20)22-13-16(18)12-21-11-15-5-3-2-4-6-15/h2-10,16,18H,11-13H2,1H3/t16-/m1/s1

Upstream product

• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 100-51-6 benzyl alcohol 
• 127744-30-3 methyl-(2R)-3-benzyloxy-2-benzoyloxy-propanoate 
• 127744-28-9 (S)-methyl 3-(benzyloxy)-2-hydroxypropanoate 
• 130111-08-9 (S)-3-(benzyloxy)-2-hydroxypropanoic acid 
• 4726-96-9 O-Benzyl-L-serine 
• 113826-06-5 (R)-glycidyl tosylate 
• 70987-78-9 (S)-Glycidyl tosylate 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 41274-09-3 D-3-Tosylglycerol 
• 713100-30-2 (S)-1-amino-3-(benzyloxy)propan-2-ol 
• 1623766-57-3 (S)-2-((benzyloxy)methyl)-5-methoxy-2,3,6,7-tetrahydro-1,4-oxazepine 
• 1623766-56-2 (S)-2-((benzyloxy)methyl)-1,4-oxazepan-5-one 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 119835-79-9 R-(+)-1-benzyloxy-3-phtalimidopropanol 
• 119835-81-3 R-(+)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>-2-oxo-4-methoxypyrimidine 
• 119835-82-4 R-(+)-5-benzyl-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>uracil 
• 119835-80-2 2-((S)-3-Benzyloxy-2-chloromethoxy-propyl)-isoindole-1,3-dione 
• 119835-83-5 R-(+)-5-(3'-benzyloxybenzyl)-1-<(1'-phtalimidomethyl-2'-benzyloxyethoxy)methyl>-2-oxo-4-methoxypyrimidine 

Relevant articles and documents

Tetrahydroimidazo(1,5-D)[1,4]Oxazepine Derivative

A compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof works as an mGluR2 antagonist, and is applicable as a therapeutic agent for neurological disorders related to glutamate dysfunction and diseases involving th

Preparation of optically active 1,2-diol monotosylates by enzymatic hydrolysis

An easy preparation of optically active 1,2-diol monotosylate derivatives by enzymatic hydrolysis is disclosed. Lipase PS (Burkholderia cepacia) catalyzes the hydrolysis of racemic 2-acetoxyhexyl tosylate with excellent enantioselectivity to afford the corresponding optically active compounds. In this reaction, a unique temperature effect is observed. After optimizing the reaction conditions, this procedure is widely applicable to the practical preparation of both enantiomers of various optically active compounds with high ee. Georg Thieme Verlag Stuttgart.

Stereoselective synthesis of polyhydroxyl surfactants. Stereochemical influence on Langmuir monolayers

Herein is described the synthesis of surfactants featuring polyhydroxylated head groups. Three head groups were prepared via consecutive stereoselective dihydroxylations of a diene. By coupling of these with lipophilic tail groups six novel surfactants have been prepared. The monolayers prepared from four of these have been investigated at the air-water interface. Significant differences were observed between monolayers consisting of enantiomerically pure surfactants contra racemates as well as between diastereomers.