Cyclopropyl based O- and N- and S-protecting groups

Details Cyclopropyl based O- and N- and S-protecting groups Cyclopropyl based O- and N- and S-protecting groups

1994-03-31

1996-07-16

Russel, Jeffrey E.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530336, 530337, 5483391, 548496, 562445, 562557, 562560, 562562, 562563, 562567, 562570, 562571, 562573, C07C22906, C07C22912, C07C32104, C07K 106

Patent

active

055368158

ABSTRACT:
The present invention is directed to the use of a cyclopropylmethyl derivative as a protecting group for compounds containing an amino group, carboxy group, amido group, mercapto group or hydroxy group and to the compounds formed having the cyclopropylmethyl moiety as the protecting group.

REFERENCES:
patent: 4565819 (1986-01-01), Vincent et al.
patent: 4622417 (1986-11-01), Barnett et al.
patent: 4638071 (1987-01-01), Barnett et al.
patent: 4692512 (1987-09-01), Janusz
patent: 4692513 (1987-09-01), Blum et al.
patent: 4781927 (1988-11-01), Zanno et al.
Brady et al. "Some Novel, Acid-Labile Amine Protecting Groups", Journal of Organic Chemistry, 1977, 42, 143-146.
J. Med. Chem., vol. 35, No. 6, Issued 1992, Olken et al., "N.sup.G -Allyl-- and N.sup.G -Cyclopropyl-L-Arginine", pp. 1137-1144.
W. J. Close (1956) "An Improved Synthesis of Cyclopropyl Phenyl Ketone and Related Substances", JACS 79, 1455-1458.
Louis A. Carpino (1993) "1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive", J. Am. Chem. 115, 4397-4398.
Eckenberg et al. (1993) "A Useful Application of Benzyl Trichloroacetimidate for the Benzylation of Alcohols", Tetrahedron 49, 1619-1624.
Timberlake et al. (1986) "Synthetic Routes to Cyclopropyl-Substituted Azoalkanes. Some Reactions of Cyclopropylcarbinyl Cyanates, Isocyanates, Benzoates, and p-Nitrobenzoates", J. Org. Chem. 33, 4054-4060.
William D. Lubell et al. (1988) ".alpha.-Amino Acids as Chiral Educts for Asymmetric Products. Alkylation of N-Phenylfluorenyl .alpha.-Amino Ketones. Synthesis of Optically Pure .alpha.-Alkyl Carboxylic Acids", J. Am. Chem. Soc. 110, 7447-7455.
A. I. Meyers et al. (1978) "Asymmetric Synthesis of (+) or (-)-2-Methyloctanal via the Metallocnamines of Chiral Alkoxy Amines", J. Org. Chem. 43, 892-898.
Brown et al. (1977) "Structural Effects in Solvolytic Reactions. 19. the Relative Electron Releasing Capability of Methyl, Phenyl, and Cyclopropyl Groups as Measured by the Tool of Increasing Electron Demand", J. Org. Chem. 42, 1073-1076.
Carpino et al. (1990) "(9-Fluorenylmethyl)oxy)carbonyl (FMOC) Amino Acid Fluorides. Convenient New Peptide Coupling Reagents Applicable to the FMOC/tert-Butyl Strategy for Solution and Solid-Phase Syntheses", J. Am. Chem. Soc. 112, 9651-9652.
Carpino et al. (1989) "Investigation of the Reaction between Amino Acids or Amino Acid Esters and 9-Formylfluorene and Its Equivalents. Possible Utility of the Derived Enamines as Amino Group Protectants", J. Org. Chem. 54, 4302-4313.
Carpino et al. (1989) "Tris(2-aminoethyl)amine as a Substitute for 4-(Aminomethyl)piperidien in the FMOC/Polyamine Approach to Rapid Peptide Synthesis", J. Org. Chem. 55, 1673-1675.
Akaji et al. (1990), "Fmoc-based Solid-phase Peptide Synthesis using a New t-Alcohol Type 4-(1',1'-dimethyl-1'-hydroxypropopyl)phenoxyacetyl Handle (DHPP)-Resin (Fmoc=fluoren-9-ylmethoxycarbonyl)", J. Chem. Soc., 584-586.
Pocar et al. (1975) "Enamines-XXXIX Enamines from Cyclopropylketones", Tetrahedron 31, 2427-2429.

Affiliated with

Also associated with

Rating

Cyclopropyl based O- and N- and S-protecting groups does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cyclopropyl based O- and N- and S-protecting groups, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclopropyl based O- and N- and S-protecting groups will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1785355