DL-Mannitol

The first, total synthesis of sugar-like compounds was performed as early as 1861 in that year, Butlerov2 reported the formation of methylenitan on treatment of aqueous formaldehyde with calcium hydroxide. The first, defined sugar derivative, DL-mannitol ( a-acrit ), was obtained by Emil Fischer and Tafel,3 and the first, optically active, totally synthetic sugars, D- and L-mannose and D- and L-fructose, were also prepared by Fischer.4... 

Grindley, T.B. McKinnon, M.S. Wasylishen, R.E. Towards understanding carbon-13 NMR chemical shifts of carbohydrates in the sohd state. The spectra of D-mannitol polymorphs and of DL-mannitol. Carbohydr. Res. 1990, 197, 41-52. 

Hexa- O -acetyl-DL-mannitol, M-25 Hexa-O-acetyl-a-robinobiosyl bromide, R-28... 

Cyclitols, Alditols, and otho Acyclic Derivatives.—epi-Inositol.SrClj/ dl-mannitol, ° l,3,4,6-tetra-0-acetyl-2,5-0-methylene-D-mannitol/ o-mannitol l,2 3,4 5,6-tris(phenylboronate)/ l-(l-S-ethyl-l-thio-D-arabinitol-l-yl)-5-fluorouracil and its 2, 3, 4, 5 -tetra-acetate/ 4,5,6-tri-0-benzoyl-2,3-di S-ethyl-... 

DL-Mannitol (a-acritol) has been obtained by the reduction of a-acrose (see p. 104). Divinylglycol from acrolein was the starting point of Lespieau and Wiemann (4S). The glycol was obtained from acrolein by reduction with the zinc-copper couple and was then oxidized with silver chlorate and osmium tetroxide to DL-mannitol. Allitol was obtained simultaneously. It is apparent, therefore, that this divinylglycol must be a mixture of diols in which the hydroxyls are cis and trans. 

Another interesting synthetic approach which also constitutes a total synthesis was accomplished by Pace (4 ). Sodium acetoacetic ester was oxidized with iodine, the product saponified, and carbon dioxide eliminated to give 2,5-hexanedione. The diketone was reduced to the diol, which was transformed to the dibromide. The hexadiene was formed and converted to the tetrabromide and subsequently to the hexabromide, which upon treatment with alcoholic potassium hydroxide gave DL-mannitol. 

A case report of acute arsine poisoning in which a 27-y-old man was exposed to arsine during chemical manufacturing was reported by Pinto (1976). The subject was exposed to arsine as a result of arsine production via a reaction between a galvanized bucket and an arsenic-containing sulfuric acid solution. The exposure (duration not specified) produced toxic effects characterized by abdominal cramping, thoracic discomfort, and hematuria. Over the next week, the patient s hematocrit declined from 42.5 to 27.1 and hemoglobin dropped from 14.1 to 9.5 g/dL even with medical intervention (blood transfusions and mannitol diuresis). Nine hours after exposure, blood arsenic was 159 g/dL and urinary arsenic was 1862 ug/L. 

DL-galactonic acid (39). 1,4-Anhydro-DL-talitol (3,6-anhydro-DL-altritol) (40) gave 2-0-(carboxymethyl)-DL-threaric acid (41) and 1,4-anhydro-D-mannitol (42) gave 2-0-(carboxymethyl)erythraric acid (43). 

The competitive inhibition of aldolase by a number of structural analogs of D-ftuctose 1,6-diphosphate has been investigated.120 Among these analogs were 1,4-anhydro-DL-ribitol 5-phosphate, 1,4-anhydro-DL-xylitol 5-phosphate, 1,4-anhydro-D-arabinitol 5-phosphate, 2,5-anhydro-D-mannitol 1,6-diphosphate, and 2,5-anhydro-D-glucitol 1,6-diphosphate. Their respective, enzyme-inhibitor,... 

The preparation of a number of a,b>-dimethanesuIfonates of alditols has been described. For example, by treating l,2 5,6-dianhydro-3,4-di-O-isopropylidene-D-mannitol with methanesulfonic acid, 1,6-di-0-(methylsulfonyl)-D-mannitol was formed. It is noteworthy that treatment of l,2-anhydro-3-deoxy-DL-glycerol with p-toluenesulfonic acid gave 3-deoxy-l-O-p-tolylsulfonyl-DL-glycerol and 3-deoxy-2-O-p-tolylsulfonyl-DL-glycerol. 

Pentostatin. Pentostntin, 2 -deoxycoformycin. dCF. NSC-218321. (/f )-3-(2-deoxy-.a-o-crylhropcntofurano.syl)-3.6.7.8-teirahydroimida7,o(4..3-dl .3 diazepin-8-ol. This compound is obtained from extracts of Sirepiamytf.s nnlihi-and formulated in lO-mg vials as a lyophilized powder. Mannitol (.30 mg) and sodium hydnixidc (to adjust pH) are included. It is administered intravenously, usually as short infusions in isotonic. solutions. Pento.statin exhibits first-order, two-compartment excretion behavior. ... 

Hyponatremia occurs with an increased amount of other solutes in the ECF, causing an extracellular shift of water or intracellular shift of Na. to maintain osmotic balance between the ECF and ICF compartments. The most common cause of this type of hyponatremia is severe hyperglycemia. As a general rule, the Na" decreases —1.6 mmol/L for every 100 mg/dL increase of glucose above 100 mg/dL. The clinical use of mannitol for osmotic diuresis can have a similar effect. 

Leuprolide acetate IM (microsphere suspension) After reconstitution 0.13% Gelatin 6.6% dl-Lactic and glycolic acid copolymer 13% Mannitol 0.2% Polysorbate 80 1% Carboxymethylcellulose in WFI... 

D-l-Deoxy-l-fluoroglycerol 3-phosphate (59), a potential anticancer agent, has been prepared from D-mannitol (60) by a stereospecific route which should be suitable for the synthesis of the L-isomer of (59).i 8 Transformation of (60) into D-l-tosyl-2,3-0-isopropylideneglycerol, followed by displacement of tosyl ion by fluoride ion, removal of the isopropylidene group, and treatment with dibenzyl phosphorochloridate gave the dibenzyl ester of (59). A DL-mixture of this dibenzyl ester was... 

Initial treatment of the acute phase of lead intoxication involves supportive measures. Prevention of further exposure is important. Seizures are treated with diazepam or phenytoin (see Chapter 19), fluid and electrolyte balances must be maintained, and cerebral edema is treated with mannitol and dexamethasone or controlled hyperventilation. The concentration of lead in blood should be determined or at least a blood sample obtained for analysis prior to initiation of chelation therapy. Chelation therapy is indicated in symptomatic patients or in patients with a blood lead concentration in excess of 50-60 pg/dL (about 2.5 pM). Four chelators are employed edetate calcium disodium (CaNa EDTA), dimercaprol, D-penicillamine, and succimer (2,3-dimercaptosuccinic acid [DMSA], chemet). CaNa EDTA and dimercaprol usually are used in combination for lead encephalopathy. 

Likewise, oxidation of 3-0-benzoyl-l,2 5,6-di-0-isopropylidene-D-mannitol with chromium trioxide in pyridine yielded crystalline 4-0-benzoyl -1,2 5,6 - di - O - isopropylidene -keto-o- arabino-3-hexulose (117). Oxidation of 6-0-benzoyl-l,2 4,5-di-0-isopropylidene-DL-ga-lactitol with chromium trioxide in pyridine gave crystalline 6-0-benzoyl-l,2 4,5-di-0-isopropylidene-fceto-DL-xi/7o-3-hexulose (118). 

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