Glycidyl (R)-(-)-4-nitrobenzenesulfonate

Glycidyl (R)-(-)-4-nitrobenzenesulfonate - Names and Identifiers

Name	(R)-(-)-Glycidyl-4-nitrobenzenesulfonate
Synonyms	Glycidyl (R)-(-)-4-nitrobenzenesulfonate (R)-(-)-Glycidyl-4-nitrobenzenesulfonate (R)-Oxiran-2-ylmethyl 4-nitrobenzenesulfonate Benzenesulfonic acid, 4-nitro-, (2R)-2-oxiranylMethyl ester
CAS	123750-60-7
InChI	InChI=1/C9H9NO6S/c11-10(12)7-1-2-9(17(13,14)15)6(3-7)4-8-5-16-8/h1-3,8H,4-5H2,(H,13,14,15)/p-1/t8-/m1/s1

Glycidyl (R)-(-)-4-nitrobenzenesulfonate - Physico-chemical Properties

Molecular Formula	C9H9NO6S
Molar Mass	259.24
Boling Point	60-62℃
Appearance	White solid
Storage Condition	2-8℃
Refractive Index	1.64
MDL	MFCD08460169

Glycidyl (R)-(-)-4-nitrobenzenesulfonate - Reference Information

Use

(R)-(-)-p-nitrobenzene sulfonic acid glycidyl ester is commonly used as an intermediate in pharmaceutical chemistry and organic synthesis, such as for calcium The synthesis of receptor antagonists. In organic synthesis and transformation, the epoxy structure in the structure can undergo ring-opening functionalization reaction under the attack of nucleophiles; in addition, the sulfonic acid in (R)-(-)-p-nitrobenzene sulfonic acid glycidyl ester The ester structure is also a good leaving group, and it can also be attacked by nucleophiles under appropriate reaction conditions to obtain derivatized chiral epoxy compounds.

synthesis method

(R)-(-)-p-nitrobenzene sulfonic acid glycidyl ester The synthesis method is as follows: slowly add triethylamine (3.75ml) to the solution of (2S)-glycidyl (27mmol) in dichloromethane (25ml) at 0 ℃, then add 4-nitrobenzenesulfonyl chloride (27mmol) solution of dichloromethane (13 ml) to the reaction mixture, and it is necessary to pay attention to the speed of addition so that the temperature does not exceed 15°C. After reacting at 0°C for 1 hour, the reaction solution is restored to room temperature, and then the solution is kept at zero for reaction overnight, the reaction mixture is concentrated, and the residue is purified by column chromatography (0-60% EtOAc/hexane) can be obtained.
Figure (R)-(-)-synthesis route of p-nitrobenzene sulfonic acid glycidyl ester

Last Update：2024-04-10 22:29:15