68938-62-5

Usage

InChI:InChI=1/C16H18O5S/c1-13-7-9-16(10-8-13)22(18,19)21-12-14(17)11-20-15-5-3-2-4-6-15/h2-10,14,17H,11-12H2,1H3

Upstream product

• 538-43-2 3-phenoxy-1,2-propanediol 
• 122-60-1 Phenyl glycidyl ether 
• 546-68-9 titanium(IV)isopropoxide 
• 3087-39-6 titanium(IV) tert-butoxide 
• 5593-70-4 titanium (IV) butoxide 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 187982-10-1 C₂₁H₂₆O₆S 
• 127840-19-1 Acetic acid (R)-1-phenoxymethyl-2-(toluene-4-sulfonyloxy)-ethyl ester 

Relevant academic research and scientific papers

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

Further improvements of the dibutyl tin oxide-catalyzed regioselective diol tosylation

In this Letter, we report that selective monotosylation of a 1,2-diol is possible using only 0.1 mol % of Bu2SnO. More interestingly, we found that the corresponding tin acetal 3b gave faster conversions and more reproducible reaction times. Moreover, the loading of this catalyst could be as low as 0.05-0.005 mol %.

Naphthyloxy acetic acid derivatives and a pharmaceutical composition comprising them as an active ingredient

The naphthyloxyacetic acid derivatives of the formula (I) wherein A is H, -(alkylene)COOR1, -(alkylene)CONR2R3, -(alkylene)OH, -(alkylene)tetrazole, -(alkylene)CN; E is single bond or alkylene; G is —S—, —SO—, —SO2—, —O— or —NR4—; L is alkylene, —(CH2)m—CH═CH—(CH2)n— or —(CH2)x—CH(OH)—(CH2)y—; M is phenyl, phenyl(thio, oxy, amino), diphenylmethyl, diphenylmethyl(thio, oxy, amino), and pharmaceutical composition comprising them as an active ingradient. The compounds of the formula (I) can combine PGE2receptor and exhibit the activity to antagonize or agonize for PGE2receptor. Therefore, they are useful as anti-hyperlipemia, for the prevention of abortion, for analgesics, as antidiarrheals, sleep inducer, diuretic, anti-diabetes, abortient, cathartics, antiulcer, anti-gastritis or antihypertensive etc.

ALKOXYLATION OF SUBSTITUTED OXIRANES BY ALKOXYTITANIUN TOSYLATES

Under mild conditions alkoxytitanium tosylates convert substituted oxiranes into the monoethers of 1,2-glycols with high regioselectivity.

A CHEMOENZYMATIC ACCESS TO OPTICALLY ACTIVE 1,2-EPOXIDES

Lipase-catalyzed transacylation in organic media was employed to produce optically active α-hydroxy tosylate which could be readily converted to the corresponding 1,2-epoxides with high optical purity.

Reaction of Terminal Oxiranes With Arenesulfonic Acid

The reaction of oxiranes 1 with arenesulfonic acids under phase transfer catalyst system (water/dichloromethane) or without catalyst (dry dichloromethane) affords regioisomeric arylsulfonyloxy primary and secondary alcohols.The latter is oxidized to 1-arylsulfonyloxy-2-alkanones 5 in good yield.