Fig. 4.

Synthesis of glycolipids. Reagents and conditions were as follows. a, 22, TMSOTf, 67%. b, (i) TFA, DCM; (ii) HBTU, myristic acid or (S)-2-acetoxymyristic acid, n-morpholine, ≈92%, two steps. c, H₂, 20% Pd(OH)₂, (ii) LiOH, H₂O:THF:MeOH, 38%, two steps. d, 26, TMSOTf, 60%. e, (i) TFA, DCM, (ii) HBTU, myristic acid or (S)-2-acetoxymyristic acid, n-morpholine, ≈92%, two steps. f, (i) NaOMe, MeOH, (ii)Pd/C, H₂, EtOH, 90%, two steps. g, 30, TMSOTf, 62%. h, (i) TFA, DCM, (ii) HBTU, nervonic acid, n-morpholine, 60%, two steps. i, (i) NaOMe, MeOH, quant; (ii) Bu₂SnO, MeOH; (iii) Me₃N·SO₃, THF, 95%. j and k, (i) LDA, TMSOOTMS, (ii) H⁺, MeOH, 30%, two steps; then LiOH, H₂O:MeOH, 81%; l, novozyme 435, CH₂=CHOAc, 54% based on S isomer.