合成路线1

The oxidative cleavage of sodium erythorbate (I) with H2O2 and NaHCO3 gives the chiral dihydroxytetrahydrofuranone (II), which is regioselectively monotosylated with Ts-Cl and pyridine to yield tosylate (III). The cyclization of (III) by means of NaOMe in methanol affords the epoxide (IV), which is opened with NaOH and NH3 in methanol to provide the dihydroxy aminoester (V). The reaction of (V) with Cbz-Cl and NaHCO3, followed by hydrolysis with HCl, gives the N-protected amino acid (VI), which is treated with Ts-OH in water to yield the lactone (VII). The reduction of (VII) with Ca(BH4)2 in methanol affords the trihydroxy compound (VIII), which is acetalyzed with acetone and PPTS to provide the protected alcohol (IX). The reaction of (IX) with Ms-Cl and TEA in toluene gives the mesylate (X), which by reaction with thiophenol and K2CO3 in DMF yields the thioether (XI). The hydrolysis of (XI) with HCl in hot methanol affords the glycol (XII), which is treated with SOCl2 and TEA in dichloromethane to provide the cyclic sulfite (XIII). Finally, this compound is cleaved with LiCl in DMF and hydrolyzed with aqueous HCl to give rise to the target (2S,3R)-3-(benzyloxycarbonylamino)-1-chloro-4-(phenylsulfanyl)-2-butanol (XIV).