79378-71-5

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 536-57-2 p-toluene sulfinic acid 

Downstream Products

• 59532-34-2 (S_S,S_S)-1,1-bis(p-tolylsulfinyl)methane 
• 140174-84-1 (E)-(S)-1-(Toluene-4-sulfonyl)-hex-1-en-3-ol 
• 140225-23-6 (E)-(S)-1-(Toluene-4-sulfonyl)-oct-1-en-3-ol 
• 169125-77-3 (R_S,S_C)-(E)-1-(p-tolylsulfinyl)-1-buten-3-ol 
• 169125-80-8 (R_S,S_C)-(E)-4-methyl-1-(p-tolylsulfinyl)-1-penten-3-ol 
• 169125-78-4 (R_S,S_C)-(E)-1-(p-tolylsulfinyl)-1-penten-3-ol 
• 169125-79-5 (R_S,S_C)-(E)-1-(p-tolylsulfinyl)-1-hexen-3-ol 
• 169125-82-0 (R_S,S_C)-(E)-1-(p-tolylsulfinyl)-1-octen-3-ol 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 40723-30-6 (+)-(S)-allyl-p-toluenesulphinamide 
• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 

Relevant academic research and scientific papers

An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine

An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos

ASYMMETRIC SYNTHESIS OF ALKYL AND ARYL SULFINATES OF DAG; AN IMPROVED AND GENERAL ROUTE TO BOTH ENANTIOMERICALLY PURE SULFOXIDES

A short, efficient and general route for the preparation of o.p. alkyl and aryl sufinates is described.Both epimers at sulfur can be obtained using DAG as unique inductor of chirality and, only by choosing the adequate base (Py or -Pr2NEt), the configu

Asymmetric Synthesis of Alkane- and Arenesulfinates of Diacetone-D-glucose (DAG): An Improved and General Route to Both Enantiomerically Pure Sulfoxides

Diacetone-D-glucose (DAG), a commercially available, sugar-derived secondary alcohol, was found to react with alkane- and arenesulfinyl chlorides in the presence of a tertiary amine in a very useful manner.When i-Pr2NEt is used as the base, (-)-(S)-alkane- and arenesulfinates are obtained in 50-90percent yield with 89 - >/= 95percent de.Simply changing the base from i-Pr2NEt to Py affords (+)-(R)-alkane- or arenesulfinates in 56-87percent yield with 70 - >/= 95percent de.The de's were determined by (1)H NMR.Optically pure alkane- and arenesulfinates are obtained either by recrystallization or by column chromatography.These sulfinates were transformed into various enantiomerically pure sulfoxides (alkyl alkyl or alkyl aryl) by reaction with different Grignard reagents.This new methodology is cheap, quick, and very convenient when both enantiomers of a given sulfoxide are needed enantiomerically pure.The influence of the solvent, as well as the effect of other types of bases, on the stereochemical course of the reaction has been evaluated, and a possible origin of the diastereoselectivity is discussed.Other optically pure secondary alcohols are used in the same reaction, and the comparison of their behavior with that of DAG is also reported.

O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU

Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates is suggested.

O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide

Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.

Preparation of Arsenesulfinic Esters of 1,2:5,6-Di-O-cyclohexylidene-α-D-glucofuranose, and Their Conversion into Optically Active Sulfoxides

Arsenesulfinyl chlorides react readily with 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose in the presence of pyridine to afford the corresponding arenesulfinates.The ratio of diastereoisomeric sulfinates formed exceeds 2:1 with the major diastereoisomer

Sugar Tosylates via p-Toluenesulfinic Acid Esters. - p-Toluenesulfinimidazolide - A Reagent for Formation of Sulfinic Acid Esters without Using Halides

The reaction of the protected sugar derivatives 1, 4, 7, 10, 13, 16, 19 and 20 with p-toluenesulfinimidazolide prepared from p-toluenesulfinic acid and N,N'-carbonyldiimidazole yields the corresponding p-toluenesulfinic esters 2, 5, 8, 11, 14, 17, 20 and 22.With the exception of 20 and 22, these products can be oxidized with m-chloroperbenzoic acid in high yields and short overall reaction times to the tosylates 3, 6, 9, 12, 15 and 18.