Lactose lactone derivative

Lactobionic acid. This derivative is produced by oxidation of the free carbonyl group of lactose (Figure 2.25), chemically (Pt, Pd or Bi), electro-lytically, enzymatically or by fermentation. Its lactone crystallizes readily. Lactobionic acid has found only limited application its lactone could be used as an acidogen but it is probably not cost-competitive with gluconic acid-<5-lactone. It is used in preservation solutions for organs prior to transplants. 

In the synthesis of n-altrose from D-ribose, first effected by Levene and Jacobs, the only crystalline intermediate was the characteristic calcium D-altronate -3.5 H2O. The sirupy lactone prepared from it was then reduced to n-altrose with sodium amalgam, as mentioned earlier in this review. Calcium n-altronate has been obtained from other sources also, such as the aluminum chloride rearrangement of the acetates of lactose, cellobiose and glucose and subsequent transformation of the neolactose, celtrobiose and altrose derivatives thus produced (see Section... 

Di-O-methy1-glucose, required for the synthesis of mycobacterial oligosaccharides, has been obtained from D-glucurono-6,3-lactone via its l,2- -isopropylldene-5- -(tetrahydropyran-2-yl) or -(1-methoxyethyl)-derivatives, which were reduced (LiAlH j) and methylated. 2 - -Methyl, 2 -0-benzyl, and 2 ,6 -di- -methyl ethers of lactose were obtained by alkylation of the two products of isopropylidenation of lactose with acidic 2,2-dimethoxypropane... 

The preparation of the octa-Q-benzoyl-aldobiononitriles of cellobiose, gentiobiose, lactose, and maltose from the unprotected oximes has been effected by treatment with benzoyl chloride in pyridine at SO C. Reaction of melibiononitrile perbenzoate with methanolic ammonia yielded the 1,1-dibenzamido-derivative (37) as the major product, isolated in 38% yield.The erythro- and threo-cyanohvdrins (38) were obtained in a 4 1 ratio from 2,3-Q-isopropylidene-D-glyceraldehyde on reaction with trimethylsilyl cyanide, and were converted to the four carbon lactone synthons (39). The chiral hexane-1,6-dinitrile (40) has been synthesized CHjOH... 

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