Synthetic Communications

doi: 10.1081/SCC-120039505pmid: N/A

Synth. Commun. 2004, 34, 2313 Synthesis of Peptidyl Ureas Using p‐Nitrophenyl‐(9‐Fluorenylmethoxycarbonylamino) Methyl Carbamate Basanagoud S. Patil, Ganga‐Ramu Vasanthakumar, and V. V. Suresh Babu* Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore, India An efficient synthesis of p‐nitrophenyl‐(9‐fluorenylmethoxycarbonylamino)methyl carbamate derivatives and their utility for the preparation of dipeptidyl ureas has been described.

Patil, Basanagoud S.; Vasanthakumar, Ganga‐Ramu; Babu, Vommina V. Suresh

doi: 10.1081/SCC-120039483pmid: N/A

Abstract An efficient synthesis of p‐nitrophenyl‐(9‐fluorenylmethoxy carbonylamino) methyl carbamates using isocyanates derived from Fmoc‐amino acid azides and p‐nitrophenol in presence of an equimolar quantity of N‐ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their utility for the synthesis of dipeptidyl ureas has been demonstrated.

Pandey, Rajesh K.; Upadhyay, Rajesh K.; Shinde, Sandip S.; Kumar, Pradeep

doi: 10.1081/SCC-120039484pmid: N/A

Abstract An efficient synthesis of (−)‐mintlactone has been described starting from (+)‐pulegone and employing the intramolecular Wittig–Horner reaction as the key step.

Telvekar, Vikas N.; Akamanchi, Krishnacharya G.

doi: 10.1081/SCC-120039485pmid: N/A

Abstract Glycosidic nitriles of protected carbohydrates were prepared efficiently and rapidly from the corresponding oximes using thionyl chloride/benzotriazole combination as dehydrating system.

Movassagh, Barahman; Mossadegh, Amir

doi: 10.1081/SCC-120039486pmid: N/A

Abstract Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. These thiolate anion species then react with alkyl tosylates to give sulfides in high to excellent yields.

Ray, S.; Srivastava, Neeta; Sangita, ; Kumar, Atul

doi: 10.1081/SCC-120039487pmid: N/A

Abstract Synthesis of substituted diaryl‐naphth‐1‐yl‐methane has been carried out by Friedel–Crafts reaction of aryl naphth‐1‐yl methanol with substituted phenols. During the course of this reaction using AlCl3 as catalyst some rearrangements occurred, resulting in the formation of a complex mixture of products. Use of CTMS, ZrCl4, and SnCl4 as a co‐catalyst in combination with AlCl3 enhanced the formation of the para alkylated product. #CDRI communication no. 5602.

Das, Satya Sandhya; Nath, Utpal; Deb, Dibakar; Das, Pranab J.

doi: 10.1081/SCC-120039488pmid: N/A

Abstract Tetra‐n‐propyl and tetra‐n‐butylammonium bromates were used for the oxidation of a variety of aromatic amines to nitro compounds. Reaction condition and recovery simple and yield of products high.

Kulkarni, Mukund G.; Kate, Sandesh D.

doi: 10.1081/SCC-120039489pmid: N/A

Abstract The regioselective 3‐O‐alkylation of 5,6‐O‐isopropylidene‐L‐ascorbic acid is achieved under mild conditions using CsF as a base. #See Ref.1.

Clososki, Giuliano C.; Missio, Lauri J.; Comasseto, João V.

doi: 10.1081/SCC-120039490pmid: N/A

Abstract (R)‐(+)‐γ‐Jasmolactone (1b) was synthesized in 92% ee in two steps, starting from the easily prepared (S)‐(−)‐3‐(5‐oxo‐tetrahydro‐furan‐2‐yl)‐propionic acid benzyl ester (2). The key step features an inversion of configuration of the stereogenic center.

Salerno, Charles P.; Cleaves, Henderson J.

doi: 10.1081/SCC-120039491pmid: N/A

Abstract α‐Methyl nitrobenzyl compounds have demonstrated superior photochemical release properties when compared to nitrobenzyl compounds lacking α‐methyl substitution at the benzylic position. The synthesis of 4‐(1‐hydroxy‐ethyl)‐3‐nitro‐benzoic acid ethyl ester and 4‐(1‐amino‐ethyl)‐3‐nitro‐benzoic acid ethyl ester was each carried out in four steps. The efficient oxidation of 4‐ethyl‐3‐nitro‐benzoic acid to 4‐acetyl‐3‐nitro‐benzoic acid by 3 mol% chromium trioxide/periodic acid in acetonitrile provides a common, crystallizable precursor from which both hydroxy and amine substituted α‐methyl nitrobenzyl compounds may be synthesized. This oxidative methodology will be useful in synthesizing a broad array of nitrobenzyl protecting groups.