D-Tartaric add

The anhydrous d-tartaric add was obtained from Matheson, Coleman and Bell, East Rutherford, New Jersey. 

Frankland and Price were the first to attempt the resolution of alcohols (and adds) by fractional crystallization of their solid esters. The isomeric solid esters formed from Z-s-butylcarbinol and di-dibenzoyl-glyceric acid failed to separate on crystallization the correspondinjg di-alcohol-i-add ester was liquid. Marckwald and McKenzie effected partial resolutions of di-mandelic add and related adds with i-menthol and d-bomeol, and of di-2-octanol with d-tartaric add, but did not develop a satisfactory method for resolving alcohols. Later investigators, however, have employed the following resolving agents in several more or less successful resolutions of certain alcohols (a) i-menthyl isocyanate, (b) d-camphoric add, (c) d- or i-mandelic add, (d) d- or... 

Tartaraldehyde, nitromethane, 740 D-Tartaric add, 351, 492,838,909 DL-Tartaric acid, 760 mew-Tartaiic add, 760 meso-Tartaric dialdehyde, 634-635 Teflon, 14, 25 Teflon-Haion, 62,63 Tellurium dibromide, 348 Terephthalic add, 666, 733,1084-1085 o-Terphenyl, 780, 781 p-Terphenyl, 337,931,932,1238 o-Terphenylenemercury, 267 cifrl,8-Tetpin, 950 Terpinolene, 568 Terramycin, 1183... 

The protected butane-1,2,3,4-tetraol 15, easily available in three steps from D-tartaric add diethyl ester, was the starting material for the synthesis of (+)-phomopsohde B (Scheme 2.4). Thus, IBX (2-iodoxybenzoic acid) oxidation of the primary alcohol followed by HWE olefination with a chiral phosphonate derived from L-lactic add (not depicted) gave a,fi-enone 16. Stereoselective reduction of the ketone carbonyl and acidic deavage of the acetal moiety furnished triol 17. Selective protection of the two secondary hydroxyl groups was achieved through triple silylation with subsequent selective desilylation of the primary OTBS group. 

Several structures of the transition state have been proposed (I.D. Williams, 1984 K.A. Jorgensen, 1987 E.J. Corey, 1990 C S. Takano, 1991). They are compatible with most data, such as the observed stereoselectivity, NMR measurements (M.G. Finn, 1985), and X-ray structures of titanium complexes with tartaric add derivatives (I.D. Williams, 1984). The models, e-g, Jorgensen s and Corey s, are, however, not compatible with each other. One may predict that there is no single dominant Sharpless transition state (as has been found in the similar case of the Wittig reaction see p. 29f.). 

DiACETYL-d-TARTARIC ANHYDRIDE, 35,49 Dialuric add monohydrate, 33, 6 2,4-DlAMINO-6-HYDROXyPYRIMlDINE,... 

Fhe answer is that Pasteur started with a 50 50 mixture of the two cltiral tartaric add enantiomers. Such a mixture is called a racemic (ray-see-mic) mixture, or racemate, and is denoted either by the symbol ( ) or the prefix d,l to indicate an equal mixture of dextrorotatory and levorotatory forms. Racemic mixtures show no optical rotation because the (-1-) rotation from one enantiomer exactly cancels the (-) rotation from the other. Through luck, Pasteur was able to separate, or resolve, racemic tartaric acid into its (-i-) and (-) enantiomers. Unfortunately the fractional crystallization technique he used doesn t work for most racemic mixtures, so other methods are needed. 

When d-tartaric acid, not jnc o-tartaric acid, is heated with arseno-acetie add for a few minutes in boiling glacial acetic add solution, a substance decomposing above 250° C., and corresponding to the folloAV-ing formula, is obtain ... 

We can now end this historical journey. We have walked through the early days of stereochemistry in the company of giants. In 1949, almost exactly 100 years after the first resolution of d,Martaric add by Pasteur, the Dutchman Bijvoet (16), using x-ray diffraction, determined the actual arrangement in space of the atoms of the sodium rubidium salt of (+)-tartaric add, and thus made the first determination of the absolute configuration about an asymmetric carbon. To further complete the link with the past, Bijvoet did this work while the Director-of the van t Hoff Laboratory at the University of Utrecht. 

Colorless, lustrous crystals, or white granules or powder, d 2.32. mp 368 above this temp it dec into perchlorate and oxygen. One gram dissolves slowly in 16.5 ml water, 1.8 ml boiling water, about 50 ml glycerol almost insol in alcohol. Keep out of contact with organic mailer or other oxidizable substances. Caution Explodes with sulfuric acid inflames with explosion if triturated with any organic substances, sulfur, phosphorus, sulfite, hypophosphite, and other oxidiz-ible substances. Incompat. Iodides, tartaric add. 

A residue of d-iso lysergic acid diethylamide and d-lysergic jcid diethylamide is dissolved in a minimum quantity of methanol (wood aicohol). A 20 % solution of maleic add (or d-tartaric iicid) in methanol is added. The LSD-25 maleate or tartarate spontaneously crystallizes and is suction filtered from the solution. The fluffy needle crystals are then washed with cold methanol. 

The crystalline tartrate is made by first removing the solvent from the benzene-chloroform elute from the chromatography column. Evaporation of the solvent to a low volume under a vacuum gives a residue which is LSD free base. Dissolve this free base in about 4 ml of warm methanol for each gram of LSD free base. Then slowly add the d-tartaric acid and allow it to react in the dark for half an hour. Then dropwise with stirring add ether to the mixture. The originally clear mixture will become milky as the ether content of the solution... 

Log Poctanol/water is estimated. Salts are referred to as tartrates. The measures on this card also apply to D tartaricacid,LD>tartaric acid and fiieso-tartaric add. ... 

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