Claims
- 1. A compound of formula III
- wherein --x--y-- is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,
- R.sub.1 is hydrogen or methyl,
- X.sub.1 is hydroxy or a carboxy protecting group suitable for peptide synthesis or a carboxy activating group suitable for peptide synthesis,
- X.sub.2 is hydrogen or an N-protecting group suitable for peptide synthesis, and
- X.sub.3 is hydrogen or an O-protecting group suitable for peptide synthesis or
- (X.sub.2 +X.sub.3) is a protecting group suitable for peptide synthesis bridging the 2-N and 3-O functions or
- (X.sub.2 +R.sub.1) is a divalent N-protecting group suitable for peptide synthesis,
- and wherein the positions 2, 3 and 4 have the configuration S,R and R or R,S and S respectively.
- 2. A compound according to claim 1 in which X.sub.1 is hydroxy and X.sub.2 and X.sub.3 are hydrogen.
- 3. A compound according to claim 1 in which X.sub.1 is hydroxy or a carboxy activating group and X.sub.2 is an N-protecting group or X.sub.1 is a carboxy protecting group and X.sub.2 is hydrogen.
- 4. A compound according to claim 1 of formula III ##STR43## wherein --x--y--, R.sub.1, X.sub.1, X.sub.2, and X.sub.3 are as defined in claim 25, with the proviso that at least one of X.sub.1, X.sub.2, X.sub.3, X.sub.2 +X.sub.3 or X.sub.2 +R.sub.1 is a protecting group suitable for peptide synthesis.
- 5. A compound according to claim 1, wherein R.sub.1 and --x--y-- have the meanings given in claim 8, with the proviso that, when R.sub.1 is methyl and --x--y-- is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, the positions 2, 3 and 4 have the configuration R,S and S respectively.
- 6. A compound according to claim 2 selected from the group consisting of:
- (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-oct-6-enoic acid;
- (2R,3S,4S,6E)-3-hydroxy-4-methyl-2-methylamino-oct-6-enoic acid;
- (2S,3R,4R,6Z)-3-hydroxy-4-methyl-2-methylamino-oct-6-enoic acid;
- (2R,3S,4S,6Z)-3-hydroxy-4-methyl-2-methylamino-oct-6-enoic acid;
- (2S,3R,4R)-3-hydroxy-4-methyl-2-methylamino-octanoic acid;
- (2R,3S,4S)-3-hydroxy-4-methyl-2-methylamino-octanoic acid;
- (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid; and
- (2R,3S,4S,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid.
- 7. A compound according to claim 4 wherein X.sub.1 is hydroxy or a carboxy-activating group and the 2-N function is in N-protected form, or X.sub.1 is a carboxy-protecting group and X.sub.2 is hydrogen.
- 8. A compound according to claim 7, selected from the group consisting of:
- (4R,5S)-4-(hex-2E-en-5R-yl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4S,5R)-4-(hex-2E-en-5S-yl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4R,5S)-4-(hex-2Z-en-5R-yl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4S,5R)-4-(hex-2Z-en-5S-yl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4R,5S)-4-(2R-hexyl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4S,5R)-4-(2S-hexyl)-1-methyl-2-oxo-oxazolin-5-carboxylic acid;
- (4R,5S)-4-(hex-2E-en-5R-yl)-2-oxo-oxazolin-5-carboxylic acid;
- (4S,5R)-4-(hex-2E-en-5S-yl)-2-oxo-oxazolin-5-carboxylic acid;
- (4R,5S)-4-(hex-2E-en-5R-yl)-1,2-trimethyl-oxazolin-5-carboxylic acid;
- (4S,5R)-4(hex-2E-en-5S-yl)-1,2-trimethyl-oxazolin-5-carboxylic acid;
- (2S,3R,4R,6E)-2-(N-t.-butyloxy-carbonyl)-methylamino-3-hydroxy-4-methyl-oct-6-enoic acid;
- (2R,3S,4S,6E)-2-(N-t.-butyloxy-carbonyl)-methylamino-3-hydroxy-4-oct-6-enoic acid;
- (2S,3R,4R,6E)-2-(N-t.-butyloxy-carbonyl)-amino-3-hydroxy-4-methyl-oct-6-enoic acid; and
- (2R,3S,4S,6E)-2-(N-t.-butyloxy-carbonyl)-amino-3-hydroxy-4-methyl-oct-6-enoic acid.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1223/80 |
Feb 1980 |
CHX |
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Parent Case Info
This is a division of application Ser. No. 299,103 filed Sept. 3, 1981, now U.S. Pat. No. 4,396,542 which, is a continuation-in-part of Ser. No. 233,713 filed Feb. 12, 1981 now abandoned.
US Referenced Citations (6)
Foreign Referenced Citations (1)
Number |
Date |
Country |
1491509 |
Nov 1977 |
GBX |
Non-Patent Literature Citations (3)
Entry |
Mori et al., Tetrahedrom, 86, 87-90, (1980). |
Ko Sawai et al., Agric. Biol. Chem., 45(5), 1223-1228, (1981). |
Ruegger et al., Helv. Chim. Acta, 59(112), 1075-1092, (1976). |
Divisions (1)
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Number |
Date |
Country |
Parent |
299103 |
Sep 1981 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
233713 |
Feb 1981 |
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