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ChemicalBook CAS DataBase List (3R,4S,5S,6S)-1-AZA-5-CARBOXYL-4-HYDROXY-6-ISOPROPYL-3-METHYL-7-OXABICYCLO[3.3.0]OCTAN-2-ONE
145451-96-3

(3R,4S,5S,6S)-1-AZA-5-CARBOXYL-4-HYDROXY-6-ISOPROPYL-3-METHYL-7-OXABICYCLO[3.3.0]OCTAN-2-ONE synthesis

8synthesis methods
145451-91-8 Synthesis
METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE

145451-91-8
11 suppliers
$498.14/5MG

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Yield:-

Steps:

Multi-step reaction with 9 steps
1: 97 percent / imidazole / dimethylformamide / 3.5 h / 23 °C
2: 96 percent / TsOH / benzene / 0.5 h / Heating
3: LiBH4 / tetrahydrofuran; methanol / 24 h / 23 °C
4: DMSO, (COCl)2, Et3N / CH2Cl2 / 1.5 h / -78 °C
5: 1.) LDA / 1.) THF, -78 deg C
6: 87 percent / H2 / Pd/C / ethanol / 24 h / 23 °C
7: 90 percent / 5percent HF / acetonitrile / 9 h / 23 °C
8: 73 percent / DMSO, (COCl)2, Et3N / CH2Cl2 / 2 h / -78 °C
9: 95 percent / NaClO2, NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s) / 0.25 h / 23 °C

References:

Corey;Reichard, Gregory A. [Journal of the American Chemical Society,1992,vol. 114,# 26,p. 10677 - 10678]