(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[([3-(benzyloxy)phenyl]sulfonyl}(cyclohexyloxy)amino]-2-hydroxypropylcarbamate → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(cyclohexyloxy)[(3-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate

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A solution of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[{[3-(benzyloxy)phenyl]sulfonyl}(cyclohexyloxy)amino]-2-hydroxypropylcarbamate (131 mg, 0.193 mmol) in ethyl acetate (˜5 mL) was combined with Palladium on carbon (10 wt %, 25 mg) and reduced under an atmosphere of Hydrogen gas. After stirring for 16 hours, the reaction mixture was filtered and evaporated in vacuo to a residue. The residue was purified on a preparative TLC plate (20×20 cm, 500 μM) eluting with 3:2 ethyl acetate:hexane. The product band was removed, eluted with 3:1 methylene chloride:methanol, filtered, and evaporated in vacuo. The residue was triturated with water, filtered and dried under high vacuum to provide (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(cyclohexyloxy)[(3-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate (93 mg, 82%) as a white solid. H1-NMR (chloroform-D3): 1.28 (m, 6H), 1.67 (m, 5H), 2.06 (m, 2H), 2.96 (m, 4H), 3.09 (b, 1H), 3.87 (m, 6H), 4.19 (m, 1H), 5.01 (m, 2H), 5.69 (d, 1H), 6.60 (b, 1H), 7.23 (m, 9H). MS(ESI): 613(M+Na).

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