Reference

Dextran-linked N6-(2-isopentenyl)adenosine - a polymer-bonded antimetabolite with "breaking points"

Dextran-linked N6-(2-isopentenyl)adenosine - a polymer-bonded antimetabolite with "breaking points". Rosemeyer, Helmut; Seela, Frank (Fachbereich Org. Chem., Univ.-Gesamthochsch., Paderborn D-4790, Fed. Rep. Ger.). Angew. Chem., 96(5), 365-7 (German) 1984. CODEN: ANCEAD. ISSN: 0044-8249. DOCUMENT TYPE: Journal CA Section: 63 (Pharmaceuticals) Section cross-reference(s): 1, 33 To increase its life span in blood circulation and therefore to prevent its dispersion in the body, the antitumor N6-(2-isopentenyl)adenosine (I) was coupled to a dextran as its cyclic acetal via a S-S bridge contg. side-chain which is cleaved in vivo by reductases. (R)-2',3'-O-(3-Ethoxycarbonyl-1-methylpropylidene)adenosine [71115-74-7] was alkylated with 1-bromo-3-methyl-2-butene [870-63-3] in DMF, and the product underwent Dimroth rearrangement with 1N NaOH and sapon. to (R)-2',3'-(3-carboxy-1-methylpropylidene)adenosine [89999-88-2]. Carboxymethyldextran T 80 [9044-05-7] in H2O was reacted with cysteamine-HCl [156-57-0] at pH 4-5 in presence of N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide to a polymer [90083-11-7] which was reacted with the above carboxy compd. to give the title compd.

Preparation of optically active amino acid hydroxyaralkyl esters

Preparation of optically active amino acid hydroxyaralkyl esters. Kawabata, Takeo; Fuji, Kaoru (Tosoh Corp., Japan). Jpn. Kokai Tokkyo Koho JP 2004026736 A2 29 Jan 2004, 16 pp. (Japanese). (Japan). CODEN: JKXXAF. CLASS: ICM: C07C233-47. ICS: C07C231-12; C07B053-00; C07M007-00. APPLICATION: JP 2002-186597 26 Jun 2002. 870-63-3 and 432023-59-1 are also in the experiment. DOCUMENT TYPE: Patent CA Section: 25 (Benzene, Its Derivatives, and Condensed Benzenoid Compounds) (R)- or (S)-R2CH2CCR1[N(Boc)MOM]CO2(CH2)nC6H4OH-o [I; R1 = C1-10 alkyl, alkenyl, alkynyl, (un)substituted Ph, (un)substituted benzyl, etc.; R2 = H, OH, C1-10 alkyl, alkenyl, alkynyl, (un)substituted Ph, N-contg. heterocyclyl; n = 2-5; MOM = methoxymethyl; Boc = tert-butoxycarbonyl] are prepd. by reaction of (R)- or (S)-R1CH[N(Boc)MOM]CO2(CH2)nC6H4OH-o (II; R1, n, MOM, Boc = same as I) with strong bases at ￡-30° followed by R2CH2X (R2 = same as I; X = leaving group). (2S)-II (R1 = benzyl, n = 2) (prepn. given) was treated with KN(SiMe3)2 in THF-PhMe at -78° for 30 min and treated with MeI for 16 h to give 81% (2S)-I (R1 = benzyl, R2 = H, n = 2) with 88% ee. .