Isosorbide 2-acetate

CgHi20s 65940-93-4) see Isosorbide mononitrate isosorbide 2-acetate-5-nitrate (C(,H]iN07 39813-48-4) see Isosorbide mononitrate l-isothiucyanato-2-nitrobenzene... 

Isosorbide 2-acetate may also be prepared by transesterification of equimolar amounts of isosorbide 2,5-diacetate and isosorbide in the presence of acidic or basic catalysts (KOH or p-toluenesulfonic acid, for 1 hat 140°, and distillation104,107 of the 2-acetate at 100° at 27 kPa 89%). Subsequent esterification of the resulting isosorbide mononitrates with acyl and aroyl halides... 

S)-Naproxen Isosorbide 2-acetate (2R,3S)-4-methoxy phenylmethyl glycidate L-Valine... 

Fewer such compounds have thus far been characterized by 13C-n.m.r. spectroscopy. Thus, data were reported for isosorbide,11,21,27 isomannide,11,28 the three isohexide dimesylates,21,29 the 2-deoxy-2-iodo 5-mesylate,21 the dideoxydiiodides of isosorbide and isoidide,21,30 isomannide ditosylate, and bis(2,5-dideoxy-2,5-diphenylphosphino)isoidide,28 of mixed substituted acetates, and of monochloromonodeoxy compounds.21... 

A high-performance, liquid chromatography (h.p.l.c.) assay (reversed phase, C lg column, methanol - water- acetate buffer) for isosorbide dinitrate along with the two mononitrates in pharmaceutical formulations has been described.45 A similar method can be found in Ref. 44. 

In connection with the elaboration of specific procedures for the manufacture of both of the isosorbide mononitrates, methods were developed to shift, with high regioselectivity, the course of the acylation reaction either towards the 5 (endo) or the 2 (exo) position, depending on the conditions applied.104-106 Thus, isosorbide 5-acylates are obtained in 70-85% yield when 3 is treated with the appropriate acid anhydride in the presence of lead(II) oxide or acetate for 20 to 40 h at room temperature. To avoid transesterifications to the appropriate 2-acylate, the workup procedures, especially during the distillation, have to be conducted under strictly neutral conditions. The contrary effect, a remarkable enrichment by the isosorbide 2-acylate (up to 90%) is realized by a transesterification process mediated by a small proportion of sodium or potassium carbonate, hydroxide, or meth-oxide, which are added to the acylation mixture from isosorbide at HOMO0, and subsequent removal of the 2-acylate by vacuum distillation.104 These two regioselective acylation methods may be used for aliphatic, as well as for aromatic, carboxylic acid anhydrides. 

Sodium isosorbide 5-nitrate, containing various different proportions of crystal water, was prepared in 46% yield by adding fuming nitric acid to isosorbide dissolved in a mixture of acetic acid, acetic anhydride, and ben-... 

With this intent, the acetates (R = COCH3, 78a), carbamates (R = CONH2, 78b), sulfamates (R = S02NH2, 78c), and ethyl ethers (R = C2H5,78d) of isosorbide 2- and 5-nitrate were investigated, and found to be similar in activity to the parent compounds.146 Several isohexide nitrates further substituted by purine bases 154 were prepared as potential cardiovascular agents.143... 

Trimethylsilylation -g.c.-m.s. has been used for the determination of isosorbide-5-mononitrate (in which both the hydroxy- and nitro-functions are silylated) in human serum, modified nucleosides in human urine and zeatin and its riboside in plant tissues after separation by solid-phase extraction and h.p.l.c. fractionation. The g.c. analyses of sucrose pertrimethylsilylated monostearate isomers and homologues with different ac l chains have been investigated on packed columns. For the g.c.-m.s. of amino-containing nucleosides, the use of -dimethylaminomethylene-O-trimethylsilyl derivatives [as in compoimd (1)] has been advocated. The derivatives are formed by reaction with DMF dimethyl acetal follwed by silylation. ... 

Isosorbide esters have also been successfully tested in several non-PVC materials like cellulose acetate, sealants and rubbers and appeared to be excellent plasticisers compared with the currently used plasticisers. 

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