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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)- synthesis
- 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)-](/CAS/20210305/GIF/704910-37-2.gif)
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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)-](/CAS/20210111/GIF/704910-42-9.gif)
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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)-](/CAS/20210305/GIF/704910-36-1.gif)
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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)-](/CAS/20210111/GIF/704910-42-9.gif)
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![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)-](/CAS/20210305/GIF/704910-44-1.gif)
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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)-](/CAS/20210111/GIF/704910-42-9.gif)
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