HCID 86701110, compound → HCID 86701112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate (400 mg, 0.73 mmol) in THF (20 mL) was added methylmagnesium chloride (1 mL, 3M in THF). After stirred for 3 hours at 0-5°C., the resulting solution was quenched with saturated aqueous NH4Cl (10 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 20% ethyl acetate in petroleum ether to give compound 73 as a yellow oil (0.37 g, 90%, diasteromers' ratio is 1:4). (ES, m/z) [M+H]+ 561.0; 1H NMR (300 MHz, CDCl3) δ 7.25-7.44 (m, 10H), 6.13-6.15 (d, J=6.9 Hz, 1H), 4.73-4.78 (m, 2H), 4.54-4.68 (m, 2H), 4.28-4.49 (m, 4H), 4.07-4.25 (m, 2H), 3.75-3.97 (m, 2H), 3.12-3.17 (m, 1H), 1.54 (s, 9H), 1.22-1.24 (d, J=6.3 Hz, 3H).

Provenance & Evidence