Claims
- 1. A method for the synthesis of 1-Amino-2,5-anhydro-1-deoxy-D-glycero-D-taloheptitol comprising:
- a. reacting 3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-lactone with mesyl chloride to give the corresponding mesylate,
- b. reacting the mesylate with potassium carbonate to produce ring contraction to a tetrahydrofuran ester with inversion of configuration at C-2,
- c. reducing the tetrahydrofuran ester with lithium aluminum hydride to give a primary alcohol,
- d. esterifying the primary alcohol at C-1 with mesyl chloride to afford a mesylate,
- e. displacing the mesylate function in the mesylate with alkali metal azide, to give the corresponding azide,
- f. removing the isopropylidene protecting groups from the azide by acid hydrolysis to give the corresponding azidotetraol, and
- subjecting the azidotetraol to palladium catlyzed reductive hydrogenation to form the desired 1-amino-2,5-anhydro-1deoxy-D-glycero-D-talo-heptitol.
- 2. A method for the synthesis of 1-Amino-2,5-anhydro-1-deoxy-D-glycero-D-taloheptitol comprising:
- a. reacting 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-lactone with triflic anhydride to give the corresponding triflate followed by treating with iodide salt to give the corresponding iodide,
- b. reacting the iodide with potassium carbonate to produce ring contraction to a tetrahydrofuran ester with inversion of configuration at C-2,
- c. reducing the tetrahydrofuran ester with lithium aluminum hydride to give a primary alcohol,
- d. esterifying the primary alcohol at C-1 with mesyl chloride to afford a mesylate,
- e. displacing the mesylate function in the mesylate with alkali metal azide, to give the corresponding azide,
- f. removing the isopropylidene protecting groups from the azide by acid hydrolysis to give the corresponding azidotetraol, and
- g. subjecting the azidotetraol to palladium catlyzed reductive hydrogenation to form the desired 1-amino-2,5-anhydro-1-deoxy-D-glycero-D-talo-heptitol.
Parent Case Info
This is a division of application Ser. No. 07/954,199, filed Sep. 29, 1992 now U.S. Pat. No. 5,250,703.
US Referenced Citations (3)
Number |
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Date |
Kind |
5011929 |
Fleet et al. |
Apr 1991 |
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5101027 |
Fleet et al. |
Apr 1991 |
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5136036 |
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Non-Patent Literature Citations (5)
Entry |
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Beacham et al., Tetrahedron: Asymmetry 2 (9), 883-900 (1991). |
Cenci di Bello et al., Biochem. J. 259, 855-861 (1989). |
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Divisions (1)
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Number |
Date |
Country |
Parent |
954199 |
Sep 1992 |
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