4-hydroxymethyl -2,2-dimethyl -1,3-dioxolane

Dimethyl-4-hydroxymethyl-1.3-dioxolane Sodium hydride Hydrogen chloride... 

Step G 4-fOrtho-(2, 3 -Dihydroxypropyloxycarbonyl)-Phenyl]-Amino-8-Trifluoromethyl-quinoHne Acetonide — 100 cc of toluene were added to 80 cc of 2,2-dimethyl-4-hydroxy-methyl-1,3-dioxolane and the toluene was distilled off under reduced pressure to eliminate the water present. To the anhydrous 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane thus obtained, 0.25 gram of an oily 50% suspension of sodium hydride and then 21.3 grams of 4-... 

Romo et al. have used Lewis acids to catalyze the formation of a-silyl-/ -lactones in their synthesis of potential inhibitors of yeast 3-hydroxy-3-methyl glutaryl-coenzyme A (HMG-CoA) synthase <1998BMC1255>. In addition to various Lewis acid catalysts, a chiral promoter based on the chiral diol (l/ ,2R)-2-[(diphenyl)hydroxymethyl]cyclo-hexan-l-ol was introduced to the reaction in an attempt to improve the stereoselectivity. A variety of chiral 2-oxetanones were formed, with enantioselectivities ranging from 22% to 85%. Dichlorotitanium-TADDOL catalysts 113 and 114 have also been used in an attempt to encourage the stereoselective [2+2] cycloaddition of silyl ketenes and aldehydes (TADDOL = (—)-/ra r-4,5-bis(diphenyl-hydroxymethyl)-2,2-dimethyl-l,3-dioxolane), although this method only afforded 2-oxetanones in moderate yields and optical purity (Equation 41) <1998TL2877>. 

TADDOL trans-4,5-bis-(diphenyl-hydroxymethyl)-2,2-dimethyl- 1,3-dioxolane... 

Song / t/. have designed a series of structurally and electronically well-defined (72-symmetric chiral ketones 84-86 for use in the epoxidation of unfunctionalized olefins (max. 59% ee for /ra r-stilbene oxide) <1997TA2921>. Adam reported the synthesis and application of chiral (72-symmetric ketones 87 and 88, derived from mannitol and TADDOL, respectively, in the epoxidation of prochiral olefins (ee s up to 80.5%) (TADDOL = (-)-/ra r-4,5-bis(diphenyl-hydroxymethyl)-2,2-dimethyl-l,3-dioxolane) <1997TA3995>. 

The mass spectrum of 2,3 4,6-di-0-isopropylidene-a-L-sorhofuran-ose (3) shows fragment-ions characteristic of a quaternary hydroxymethyl group (m/e 229, 171, 130, and 115), and also those associated with 2,2-dimethyl-l,3-dioxolane rings (m/e 245, 187, 185, and 127). New fragment-ions at m/e 113 and 159 are also observed, and the mechanisms by which they are presumed to be formed are shown in Scheme XIII. With the exception of the peak at m/e 159, the spectrum... 

Tosylmethyl isocyanide (TosMIC) (217) has the potential to serve as a carbonyl equivalent. Treatment of 209 with the anion of 217 under phase-transfer conditions provides unstable (45, 5 S)-4-benzyloxymethyl-2,2-dimethyl-5-(2 -tosyl-2 -isocyanoethyl)-1,3-dioxolane (218), which is treated with lithium in liquid ammonia to afford (4 5,5iS)-4-ethyl-5-hydroxymethyl-... 

Monoalkylated TosMIC 222 reacts with 209 to furnish, after lithium—ammonia deprotection, (4 5,55)-5-pentyl-4-hydroxymethyl-2,2-dimethyl-l,3-dioxolane (223). This is smoothly converted in four steps to (4iS, 55)-5-hydroxy-4-decanolide (L-factor) (224), the proposed autoregulator isolated from mutant strains of Streptomyces grieseus [79] (Scheme 52). 

Metadioxane [505-22-6] (2,2-dimethyl-4-hydroxymethyl-l,3-dioxolane) is a high-boiling solvent with an excellent solvency for resins and polymers. It is used in printing inks, adhesives, and in the textile sector. 

Dimethyl-4-hydroxymethyl-l,3-dioxolane added to a soln. of triphenylphosphine in GGI4, warmed under reflux on a water bath to start the reaction, and heating resumed for 15 min. after the initial vigorous reaction has subsided 2,2-dimethyl-4-chloromethyl-l,3-dioxolane. Y >80%. — This rapid procedure converts alcohols to alkyl halides under mild, essentially neutral conditions. F. e. s. J. B.Lee et al., Gan. J. Ghem. 44, 1331 (1966) Ghem. Ind. 1966, 900 carboxylic acid chlorides from carboxylic acids s. Am. Soc. 88, 3440 (1966). 

Yokomatsu T, Yoshida Y, Suemune K, Yamagishi T, Shibuya S (1995) Enantioselective synthesis of threo-a,jS-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-l,3-dioxolane. Tetrahedron Asym 6 365-368... 

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