Claims
- 1. N-butyl-1,4-dideoxy-1,4-imino-D-mannitol.
- 2. N-Benzyl-1,4-dideoxy-1,4-imino-D-mannitol.
- 3. A method for the synthesis of the N-butyl or N-benzyl derivative of 1,4-dideoxy-1,4-imino-D-mannitol comprising:
- (a) catalytically hydrogenating 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol to give a corresponding diol,
- (b) chemically alkylating the diol with butanal to form a protected N-butyl derivative or with benzyl bromide to form a protected N-benzyl derivative, and
- (c) removing the isopropylidene protecting group by acid hydrolysis to give, respectively, the N-butyl or N-benzyl derivative of 1,4-dideoxy-1,4-imino-D-mannitol.
- 4. A method for the synthesis of the N-butyl or N-benzyl derivative of 1,4-dideoxy-1,4-imino-D-mannitol comprising:
- (a) displacing the primary mesylate of the dimesylate, 1,4-bis(O-methanesulfonyl)-2,3:5,6-di-O-isopropylidene-D-mannitol, by reacting said dimesylate with sodium azide to give an azidomesylate,
- (b) partially hydrolyzing the azidomesylate with camphorsulfonic acid to remove the isopropylidene protecting group at C-5 and C-6 to give a corresponding diol,
- (c) oxidizing the diol to give 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol,
- (d) catalytically hydrogenating the 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol to give a corresponding diol,
- (e) chemically alkylating the diol with butanal to form a protected N-butyl derivative or with benzyl bromide to form a protected N-benzyl derivative, and
- (f) removing the isopropylidene protecting group by acid hydrolysis to give, respectively, the N-butyl or N-benzyl derivative of 1,4-dideoxy-1,4-imino-D-mannitol.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation of application Ser. No. 07/461,859, filed Jan. 8, 1990, U.S. Pat. No. 4,996,329, which is a continuation-in-part of copending application Ser. No. 07/424,628, filed Oct. 20, 1989.
Non-Patent Literature Citations (4)
Entry |
Fleet, J. Chem. Soc. Chem. Commun. 1984, pp. 1240-1241. |
Bashyal et al., Tetrahedron 43, 3083-3093 (1987). |
Fleet et al., FEBS Lett. 237, 128-132 (1988). |
Fleet et al., Tetrahedron 44, 2649-2655 (1988). |
Continuations (1)
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461859 |
Jan 1990 |
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Continuation in Parts (1)
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424628 |
Oct 1989 |
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