Abstract
Three 2-amino-1, 3-alkanediols (alkane : decane, dodecane, and tetradecane) (4) were synthesized by the catalytic reduction of sodium salts of aci-2-nitro-1, 3-alkanediols, (3), in the presence of 5% Pd-C in glacial acetic acid at 40°C in good yields. Silylation of (4) with a mixture of HMDS and TMCS gave three compounds, O, O-bis-TMS derivative of (4) [(5)], and N, O, O-tris-TMS deriv-atives of threo- and erythro- (4) [threo- and erythro- (6)], but two ones, threo- and erythro- (6), in the case of BSA. The structures of (6) were confirmed by mass spectra. The characteristic fragment ions were m/e=204 [base peak ion : formed by the cleveage between C-2 and C-3], M-105, M-103 and M-15. The m/e values of these fragment ions were 72 larger than those of (5). Evidence for a facile determination of erythro/threo ratios of (4) by GLC was demonstrated. Erythro contents of (4) were ca. 70% in each case, in agreement with those calculated from the GLC of O, O-bis-TMS derivatives of N-acetyl- (4). Attempted separation of erythro and threo isomers of (4) were carried out by recrystallization of N, O, O-triacetyl-2-amino-1, 3-alkanediols (7) and N-acetyl-2-amino-1, 3-alkanediols (8).
