4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aR,6aS)- synthesis

6synthesis methods

Product Name:4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aR,6aS)-
CAS Number:474093-14-6
Molecular formula:C8H12O3
Molecular Weight:156.18

5-O-TERT-BUTYLDIMETHYLSILYL-2,3-O-ISOPROPYLIDENE-D-RIBOFURANOSE

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4H-Cyclopenta-1,3-dioxol-4-ol, 3a,6a-dihydro-2,2-dimethyl-, (3aR,6aS)-

474093-14-6
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Yield:-

Steps:

Multi-step reaction with 7 steps
1: 91 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 3 h / Heating
2: 75 percent / dicyclohexylcarbodiimide; CF₃CO₂H; pyridine / DMSO / toluene / 10 h / 20 °C
3: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C
4: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
5: aq. NaIO₄ / 0.58 h / 0 - 20 °C
6: 11.4 g / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C
7: Grubbs' catalyst / CH₂Cl₂ / 4 h / 24 °C

References:

Jin, Yun H.;Liu, Peng;Wang, Jianing;Baker, Robert;Huggins, John;Chu, Chung K. [Journal of Organic Chemistry,2003,vol. 68,# 23,p. 9012 - 9018]

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1,3-Dioxolane-4-methanol, α,5-diethenyl-2,2-dimethyl-, (4R,5S)-

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References