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

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

8synthesis methods

Product Name:(3R,4S,5R,6S)-1-AZA-4-HYDROXY-5-FORMYL-6-ISOPROPYL-3-METHYL-7-OXABICYCL[3.3.0]OCTAN-2-ONE
CAS Number:145452-03-5
Molecular formula:C11H17NO4
Molecular Weight:227.26

4-Oxazolidinepropanoic acid, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-β-hydroxy-α-methyl-5-(1-methylethyl)-3-(phenylmethyl)-, methyl ester, (αR,βS,4S,5S)-

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

145452-03-5
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Yield:-

Steps:

Multi-step reaction with 3 steps
1: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h
2: 48percent HF / acetonitrile / 24 h / 23 °C
3: Et₃N, oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

References:

Corey;Li, Weidong;Reichard, Gregory A. [Journal of the American Chemical Society,1998,vol. 120,# 10,p. 2330 - 2336]

145452-02-4 Synthesis