Within the following experimental procedure, click on bolded terms for additional information on various experimental techniques.

(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate 14:

Alcohol (4S, 6R, 7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-ol 13 (17.2 g, 42.8 mmol, 1.0 equiv) was stirred and (E)-5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoic acid 12 (14.0 g, 53.0 mmol, 1.2 equiv) were dissolved in CH2Cl2 (40 mL) in a 250 mL rb flask at 0 °C. 4-dimethylaminopyradine (DMAP) (7.9 g, 64.3 mmol, 1.5 equiv) and DMAP·HCl (6.8 g, 42.8 mmol, 1.0 equiv) where added to the round bottom flask to dissolve the starting materials. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (20.0 g, 128.5 mmol, 3.0 equiv) was then added.  The solution was continuously stirred for 15 hours at room temperature.  The mixture was then diluted with 400mL of 20% ethyl acetate (EtOAc)/hexanes and 300mL of distilled water. The solution was extracted with 20% EtOAc/hexanes (2 × 400 mL).  The organic layers were combined, then dried over Na2SO4, and concentrated under reduced pressure.  The organic layers were purified using flash column chromatography in a 10 × 12 cm silica gel column and eluted with 10% EtOAc/hexanes. Increments were collected using 125 mL fractions.  The fractions with product were combined and concentrated under reduced pressure to yield ester 14 (23.9 g, 87%) as a clear yellow oil. 

Rf = 0.47 (30% EtOAc/hexanes); (c = 1.0, CHCl3); 500 MHz 1H NMR (CDCl3) δ 7.35-7.25 (m, 7H), 6.88-6.84 (m, 2H), 5.86 (ddd, J = 16.2, 2.0, 2.0 Hz, 1H), 5.79 (dddd, J = 17.1, 9.8, 6.8, 6.8 Hz, 1H), 5.75 (dddd, J = 17.1, 9.8, 7.3, 7.3 Hz, 1H), 5.21 (dddd, J = 6.7, 6.7, 6.7, 3.3 Hz, 1H),  5.07-5.04 (m, 1H), 5.25-5.04 (m, 1H), 4.82 (d, J = 3.4 Hz, 1H), 4.78 (d, J = 6.8 Hz, 1H), 4.62 (ddd, J = 11.7, 11.7, 11.7 Hz, 2H), 4.52 (d, J = 10.8 Hz, 1H), 4.36 (d, J = 10.8 Hz, 1H), 4.16 (dd, J = 4.9, 1.5 Hz, 2H), 3.95 (dq, J = 6.8, 6.4 Hz, 1H), 3.79 (s, 3H), 3.43 (ddd, J = 10.3, 4.9, 2.0 Hz, 1H), 2.40-2.26 (m, 1H), 1.84-1.77 (m, 1H), 1.70-1.62 (m, 1H), 1.30 (s, 3H), 1.29 (s, 3H), 1.18 (d, J = 6.4 Hz, 3H), 0.90 (s, 9H), 0.06 (s, 6H); 125 MHz 13 C NMR (CDCl3) CH3 δ 55.4, 26.1, 25.3, 25.1, 15.4, -4.9; CH2 δ 118.0, 93.4, 73.1, 69.5, 64.0, 39.6, 34.5; CH1 δ 134.7, 133.6, 129.9, 128.6, 128.0, 127.9, 127.8, 113.9, 77.4, 73.4, 70.4; CH0 δ 175.9, 159.4, 138.0, 130.6, 128.0, 44.1; IR (neat) 2954, 2857, 1727, 1514, 1469, 1385, 1250, 1104, 1041, 836, 777 cm-1