Sodium periodate ethers

Sanchez et al. [61,62] studied the stability of sodium decyl, dodecyl, and tetradecyl sulfates and sodium lauryl ether (3 EO) sulfate in acid media (pH 1) at different temperatures and concentrations above and below the critical micelle concentration. Sodium decyl sulfate was shown to be relatively stable for several hours at temperatures up to 90°C. Sodium dodecyl and tetradecyl sulfates were only stable for short periods of time at temperatures above 40-50°C. As expected, sodium lauryl ether sulfate was less stable to hydrolysis than the corresponding lauryl sulfate. 

Pure homoallylic alcohols are converted into y-amino-p-hydroxy acids by protection as the TBDMS ether or A(0-acetonide followed by degradative oxidation of the terminal alkene using a catalytic amount of ruthenium(III) chloride and sodium periodate (Scheme... 

In a first step, the TBS ether is subjected to acid cleavage with copper sulfate in acetone containing a catalytic amount of glacial acetic acid. The resulting diol is then protected as an acetunide. Next, the double bond is oxidatively cleaved with sodium periodate and a catalytic amount of osmium tetroxide to give aldehyde 5. 

A 62 35 3 ethyl acrylate-methyl methacrylate-acrylic acid copolymer latex was prepared by continuous addition of the monomer mixture over a 4-hour period at 80° (22). The emulsifier was a sodium lauryl ether sulfate-nonylphenol polyoxyethylene adduct (20 moles ethylene oxide) mixture, the initiator a potassium persulfate-sodium hydroxulfite mixture, and the buffer a sodium bicarbonate-potassium hydroxide mixture. The final latex of pH 6.5 contained 40% solids, and the Tg of the copolymer was 13°. 

To 5.69 g of this acetal in 410 ml of t-butanol and 11 ml of water was added a mixture of 5.80 g of potassium carbonate, 22,8 g of sodium periodate, and 270 mg of potassium permanganate in 1230 ml of water. The reaction mixture was stirred at 20-25°C for 20 hours and concentrated in vacuo to remove t-butanol. Ethylene glycole (0.5 ml) was added and reaction mixture extracted with 1 1 ether-benzene to remove neutral material. The aqueous layer acidified with solid sodium dihydrogen phosphate and extracted 4 times with 1 1 ethyl acetate-benzene. The organic layer was dried over sodium sulfate and evaporated to dryness in vacuo affording (+/-)-3-acetyl-2a-(2-carboxyethyl)-5-oxo-ip-cyclopentaneheptanoic acid methyl ester, 5-cyclic ethylene acetal as a mixture of the 3a and 3p isomers. 

Boron trifluoride diethyl etherate Sodium bicarbonate Palladium on charcoal Sodium periodate Hydroperoxide, 1,1-dimethylethyl Titanium tetraisopropoxide Ethyl diisopropylamine Triethylamine Ammonium sulfate Trimethylsilyl triflate d-3-oxo-a-D-gluco-pyranoside -oxo-a-D-erythro-hexopyranoside... 

The synthesis was performed according to Scheme 9.3. 1,2-Bis (2-methyl-1-ben-zothiophen-3-yl)perfluorocyclopentene (9a) was formylated with dichloromethyl methyl ether to give diformyl compound 14, which treated with 2,3-bis(hydroxy-amino)-2,3-dimethylbutane sulfate followed by sodium periodate. Compound 10a was obtained and purified by column chromatography and gel permeation chromatography (GPC). Recrystallization from hexane-CH2Cl2 gave dark-blue plate crystals of 10a. 

When primary alkyl phenyl tellurium or secondary alkyl phenyl tellurium compounds in methanol were treated with an excess of 3-chloroperoxybenzoic acid at 20, the phenyltelluro group was eliminated and replaced by a methoxy group. This reaction, which converts alkyl halides used in the synthesis of alkyl phenyl telluriums to alkyl methyl ethers, produced the ethers in yields as high as 90%3-4 Olefins are by-products in these reactions4 With ethanol as the solvent, ethyl ethers were formed. Other oxidizing agents (hydrogen peroxide, ozone, (ert.-butyl hydroperoxide, sodium periodate) did not produce alkyl methyl ethers. 

MET-CAMO was prepared from 5/ -methylthebaine (57) [109,110] via 14/ -amino-7,8-dihydro-5/ -methylcodeinone (59) which was obtained by the Kirby-McLean procedure [111]. Thus, oxidation of 2,2,2-trichloroethyl A-hydroxycarbamate with sodium periodate in the presence of 5/ -methylthebaine gave the adduct (58). Catalytic hydrogenation using a Pd/C catalyst in methanol in the presence of sodium acetate-acetic acid buffer yielded amine (59). Reaction with 4-nitrocinnamoyl chloride furnished amide (60) and ether cleavage using boron tribromide yielded MET-... 

In a typical example, sodium periodate (18.2 g, 85 mmol) was added in small portions over a 45 min period to l,4-dioxa-6-acetyl-6-allylspiro[4.5]decane (8.9 g, 40 mmol) and osmium tetroxide (0.10 g, 0.39 mmol) in a solution of THF (126 mL) and water (42 mL) at room temperature. The mixture was stirred for 2 h at this temperature during which time the black slurry turned brown. Water (600 mL) was introduced, and the mixture was extracted with ether. The extract was dried over anhydrous magnesium sulfate and stripped of solvent to give 7.4 g of crude aldehyde. (Because osmium tetroxide is a toxic and volatile irritant, all preparations should be carried out in a fume hood with use of adequate personal protection, gloves and safety glasses.) Other examples of the use of this reagent have b n summarized in Table 5. 

Epoxidadon of (Z)-vinyl sulfone, which is available from the Peterson olefination of (S)-O-pentylideneglyceraldehyde and phenyl trimethylsilylmethyl sulfone in three steps (40% overall yield), with f-BuOOH/t-BuOK in THE gives epoxy sulfone (eq 2). Deprotection of the ketal group and recrystallization affords an optically pure epoxy diol, which is then treated with sodium periodate followed by sodium borohydride to give an alcohol. Protection of the resulting alcohol as its silyl ether yields l/ ,25)-l-phenylsulfonyl-2- [ fcrf-butyldiphenyl)silyl]oxymethyl oxirane ). Its enantiomer is available in the same manner starting from / )-isopropylideneglyceraldehyde. ... 

Overhand, Overkleeft and their collaborators have synthesised a variety of SAAs [39]. The synthesis of Fmoc-protected 6 ( Fig. 2) is illustrated in Scheme 2 [15]. Tri-O-acetyl-D-glu-cal was converted into the SAA precursor 43 in five steps. Formation of the trichloroacetimi-date derivative 44 and a subsequent Overman rearrangement was used to introduce the amino group onto the pyran scaffold giving 45. Hydrogenation of the olefin in 45 was accompanied by cleavage of the silyl ether to afford the primary alcohol which was oxidised with a catalytic amount of ruthenium (III) chloride in the presence of sodium periodate giving 46. Subjection... 

---