Zoylated derivative

Wang, T. Zhang, Z. Meanwell, N. A. Benzoy-lation of dianions preparation of monoben-zoylated derivatives of symmetrical secondary diamines./. Org. Chem. 1999, 64, 7661-7662. 

DL-Threose was prepared19 from DL-threonic acid (10) in a slightly modified way. Benzoylation of 10 yielded 2,3-di-O-benzoyl-DL-threono-1,4-lactone (lib), instead of the desired 2,3,4-tri-O-benzoyl-DL-threonic acid. When DL-threonamide (15a) was used19 as the substrate, the 2,3,4-tri-O-benzoyl derivative 15b could be readily prepared. Deamination of 15b with nitrous acid, preparation of the acid chloride, and Rosenmund reduction of the latter, followed by deben-zoylation of the product, afforded DL-threose in good yield. 

Figure 1. TLC of myelin lipids after treatment with perbenzoylation-desulfa-tion. Line S, standard line M, derivatized myelin lipids. Spots 1 through 6 are ben-zoylated-desulfated derivatives of (I) glucocerebroside, (2) nonhydroxycere-broside, (3) monogalactosyl diglyceride, (4) hydroxycerebroside, (5) nonhydroxy-sulfatide, and (6) hydroxysulfatide, respectively. See text for details of TLC conditions.

On heating, with benzaldehyde, methyl P-L-arabinopyranoside gave, after ben-zoylation, the 3,4-0-(S)-benzylidene derivative (93), whereas selective hydrolysis of a 1 1-mixture of the diastereoisomers gave the (R)-isomer 9A)V The pure isomers (93) and (94) were converted into methyl 3,4-0-(S)- and -(R)-benzylidene-p-L-ribopyranoside, respectively, on successivedebenzoylation, oxidation (DMSO-acetic anhydride), and reduction (sodium borohydride). Under anhydrous acid conditions, methyl 3,4-0-(R)-benzylidene-P-D-ribopyranoside rearranged to the... 

---