(alphaR,4S,5S)-2-(alpha-Benzoxycarbonylethyl)-4,5-dihydroxy-1,2-oxazinan-3-one → HCID 59989624, compound

Participants

Reaction Steps

A suspension of 5% Pd-C (0.137 g) in EtOAc (10 mL) was stirred for 1 h under H2 atmosphere and a solution of the benzyl ester 8a (0.137 g, 0.464 mmol) in EtOAc (15 ml) was added portionwise. The reaction mixture was stirred for 8 hours under H2 and filtered through a short pad of Silica Gel 60H (for TLC) followed by washing with MeOH (7×5 mL). After evaporation of the filtrate in vacuo, the residue was triturated with dry ether and dried in vacuo to provide 0.093 g (98%) of the product 9a as a white solid. 1H NMR (400 MHz) in CD3CN (J, Hz): δ 1.44 (3H, d, 3J=7.3, α-MeCH), 3.00 (2H, br. s, OH, OH), 3.90 (1H, m, 6-HA), 4.37 (1H, d, 3J=4.4, 4-H), 4.49-4.43 (2H, m, 6-HB, 5-H), 5.01 (1H, q, 3J=7.3, α-CH), 5.31 (1H, br. s, COOH). 13C (100 MHz) in CD3CN: δ 13.55, 54.34, 70.15, 70.64, 78.41, 171.22, 172.85.

Provenance & Evidence