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Synthesis 2005(13): 2267-2269
DOI: 10.1055/s-2005-869986
DOI: 10.1055/s-2005-869986
PSP
© Georg Thieme Verlag Stuttgart · New York
Convenient Enantiopure Synthesis of (2S,3R)-2-O-Benzyl-3,4-O-isopropylidene-d-erythritol from d-(+)-Glucono-δ-lactone: A Potential C4 Chiral Building Block
Further Information
Received
24 November 2004
Publication Date:
27 June 2005 (online)
Publication History
Publication Date:
27 June 2005 (online)
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Abstract
A new convenient synthesis of (2S,3R)-2-O-benzyl-3,4-O-isopropylidene-d-erythritol has been achieved starting from extremely cheap and commercially available d-(+)-glucono-δ-lactone. It involves two carbon excisions using ozonolysis. The inbuilt stereochemistry ensures the enantiopurity of the target compound.
Key words
lactones - eliminations - ozonolysis - reduction
- 1
Coppola GM.Schuster HF. α-Hydroxy Acids in Enantioselective Syntheses VCH-Wiley; New York: 1997. p.313 - 2
Williams DR.Moore JL.Yamada M. J. Org. Chem. 1986, 51: 3916 - 3
Dondoni A.Orduna J.Merino P. Synthesis 1992, 201 - 4
Arroyo-Gómez Y.Rodriguez-Amo JF.Santos-Garcia M.Sanz-Tajedor MA. Tetrahedron: Asymmetry 2000, 11: 789 -
5a
DeLuchi O.Miotti U.Modena G. Org. React. (N.Y.) 1991, 40: 157 -
5b
Moiseenkov AM.Dragan VA.Veselovskii VV. Russ. Chem. Rev. 1991, 60: 643 - 6
Wang Y.Babirad SA.Kishi Y. J. Org. Chem. 1992, 57: 468 - 7
Abushanab E.Vemishetti P.Leiby RW.Singh HK.Mikkilineni AB.Wu DC.-J.Sai Baba R.Panzica RP. J. Org. Chem. 1988, 53: 2598 - 8
Flasche M.Scharf H.-D. Tetrahedron: Asymmetry 1995, 6: 1543 -
9a
Regeling H.Chittenden GJF. Recl. Trav. Chim. Pays-Bas 1989, 108: 330 -
9b
Regeling H.Rouville ED.Chittenden GJF. Recl. Trav. Chim. Pays-Bas 1987, 106: 461 - 10
Rauter AP.Fernandes AC.Figueiredo JA. J. Carbohydr. Chem. 1998, 17: 1037 - 11
Flasche M. PhD Thesis RWTH Aachen; Germany: 1995.