Tris- methyl benzoate sodium

Although the reaction with thiosulfate and with iodide ions may be a mere reduction of the halide, the reaction with sodium benzoate would appear to be a radical dissociation induced by the attack of a negative ion. The fate of the benzoate ion is unknown. Tris-( -nitrophenyl)-methyl benzoate is a stable substance which does not dissociate into radicals.23... 

Esters are also reduced by sodium aluminum hydride (yields 95-97%) [<9<9] and by lithium trimethoxyaluminum hydride (2 mol per mol of the ester) [94] but not by lithium tris tert-butoxy)aluminum hydride [96], Another complex hydride, sodium bis(2-methoxyethoxy)aluminum hydride, reduces esters in benzene or toluene solutions (1.1 -1.2 mol per ester group) at 80° in 15-90 minutes in 66-98% yields [969], Magnesium aluminum hydride (in the form of its tetrakistetrahydrofuranate) reduced methyl benzoate to benzyl alcohol in 58% yield on refluxing for 2 hours in tetrahydrofuran [59]. 

O-Dechloroacetylation of IV.61 by treatment with thiomea gave IV.62, which was subsequently reprotected as the hydrogenolyzable 4-methoxybenzyl ether with 4-methoxybenzyl trichloroacetimidate and triflic acid under phase transfer catalysis conditions [104]. Saponification of the benzoate and methyl esters with lithium hydroperoxide followed by methanolic sodium hydroxide and acidification then gave the acid IV.63. O-Sulfonation of IV.63 was achieved with the sulfur trioxide-tri-methylamine complex to give the disulfate IV.64 as the sodium salt. Finally, hydro-genolysis of IV.64 with Pd/C in aqueous methanol afforded the target disaccharide IV.51. 

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