D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxo-, methyl ester, (3S,4R)- synthesis

3synthesis methods

Product Name:D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxo-, methyl ester, (3S,4R)-
CAS Number:704910-42-9
Molecular formula:C16H25NO6
Molecular Weight:327.37

1,2-Oxasilino[5,6-c]pyrrole-7-carboxylic acid, octahydro-6-[(4-methoxyphenyl)methyl]-2,2,7a-trimethyl-5-oxo-7-[(phenylmethoxy)methyl]-, methyl ester, (4aR,7R,7aS)-

704910-37-2
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D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxo-, methyl ester, (3S,4R)-

704910-42-9
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Yield:-

Steps:

Multi-step reaction with 5 steps
1: H₂ / Pd/C / ethanol / 12 h / 23 °C / 760 Torr
2: 2.68 g / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C
3: 83 percent / tetrahydrofuran / 5 h / -78 °C
4: 92 percent / KHCO₃; KF; aq. H₂O₂ / methanol; tetrahydrofuran / 18 h / 23 °C
5: 83 percent / aq. ceric ammonium nitrate / acetonitrile / 1 h / 0 °C

References:

Reddy, Leleti Rajender;Saravanan;Corey [Journal of the American Chemical Society,2004,vol. 126,# 20,p. 6230 - 6231]

D-Proline, 3-[[(bromomethyl)dimethylsilyl]oxy]-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[(phenylmethoxy)methyl]-, methyl ester, (3S)-

704910-36-1
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704910-42-9
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References

1,2-Oxasilino[5,6-c]pyrrole-7-carboxylic acid, octahydro-7-(hydroxymethyl)-6-[(4-methoxyphenyl)methyl]-2,2,7a-trimethyl-5-oxo-, methyl ester, (4aR,7R,7aS)-

704910-44-1
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704910-42-9
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References