Protection of 1,2-/1,3-Diols

Protection of 1,2-/1,3-Diols

Overall Score5
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • General Characteristics

1,2- and 1,3-diols are generally protected as 5- or 6-membered cyclic acetal compounds.

 

  • General References

・Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, H. W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53. DOI: 10.1021/cr990101j

  • Reaction Mechanism
  • Examples

Regioelective protection of D-mannitol.[1]

PG_diol_4[1]

Regioselective protection of methyl glucose.[2]

PG_diol_5[1]

  • Experimental Procedure

  • Experimental Tips

Common protective groups are shown below. Benzylidene acetals and dimethyl acetals have thermodynamic tendency to form six- and five-membered rings, respectively. This can be utilized in the regioselective protection of polyol compounds.

PG_diol_2[1]

 

Acetals are stable under basic and reductive conditions and unstable toward acids. Carbonates are deprotected under basic conditions. Silyl acetals are usually deprotected with fluoride sources.

  • References

[1] Schmid, C. R.; Bryant, J. D. Org. Synth. 1995, 72, 6.
[2] Ferro, V.; Mocerino, M.; Stick, R. V.; Tilbrook, D. M. G. Aust. J. Chem. 1988, 41, 813.

  • Related Books

 

 

 

 

 

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