✦ LIBER ✦

Total synthesis of 4-(d-alanylamino)-2-amino-2,3,4-trideoxy-dl-threo-pentose (3-deoxy-dl-prumycin)

✍ Scribed by Violetta Constantinou-Kokotou; Elias A. Couladouros; Minas P. Georgiadis; George Kokotos; Taxiarchis M. Georgiadis

Publisher: Elsevier Science
Year: 1991
Tongue: English
Weight: 726 KB
Volume: 222
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(91)89015-8

No coin nor oath required. For personal study only.

✦ Synopsis

3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-oqent-2-enopyranos~ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second axido group with inversion of configuration at C-4 afforded intermediates 14 and 17, both of which had a three configuration in regard to C-2 and C-4. Coupling with o-alanine and total deprotection yielded the title compound 1. * This paper is No. 11 in the series Products from Furans. For the previous papers, see ref. 6.

📜 SIMILAR VOLUMES

New compounds: Total synthesis of dl-3a,

New compounds: Total synthesis of dl-3a,4,6a-cis-4-(4-carboxybutyl)-hexahydropyrrolo[3,4-d]imidazol-2-one hydrochloride (dl-azabiotin hydrochloride)

✍ Henry C. Wormser; Hanley N. Abramson 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 English ⚖ 346 KB

Synthesis of dl-4ξ-(2-carboxyethyl) -cis

Synthesis of dl-4ξ-(2-carboxyethyl) -cis-hexahydropyrrolo-[3,4-d]imidazol-2-one (Bisnorazabiotin)

✍ Henry C. Wormser; Hanley N. Abramson 📂 Article 📅 1975 🏛 John Wiley and Sons 🌐 English ⚖ 339 KB

Synthesis of dl-4ξ-(4-carboxybutyl)-5-ca

Synthesis of dl-4ξ-(4-carboxybutyl)-5-carbethoxy-cis-hexahydropyrrolo-[3,4-d]imidazol-2-one (N-carbethoxyazabiotin)

✍ Henry C. Wormser; Hanley N. Abramson 📂 Article 📅 1975 🏛 John Wiley and Sons 🌐 English ⚖ 415 KB

Synthesis of 2-(3′-Azido- and 3′-Amino-3

Synthesis of 2-(3′-Azido- and 3′-Amino-3′-deoxy-β-D-ribofuranosyl)thiazole-4-carboxamide.

✍ Cheng Wu Liang; Myong Jung Kim; Lak Shin Jeong; Moon Woo Chun 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 197 KB 👁 1 views

Crystal and molecular structures of 6-O-

Crystal and molecular structures of 6-O-acetyl-2,3,4-trideoxy-α-dl-glycero-hex-2-enopyranose and 3-O-(6-O-acetyl-2,3,4-trideoxy-α-l-glycero-hex-2-enopyranosyl)-1,2;5,6-di-O-isopropylidene-α-d-glucofuranose

✍ Janusz W. Krajewski; Przemysł Gluziński; Zofia Urbańczyk-Lipkowska; Anna Banasze 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 772 KB

ChemInform Abstract: Synthesis and Prope

ChemInform Abstract: Synthesis and Properties of 1-(3,4-Di-O-acetyl-2-deoxy-2-hydroxyimino-D-threo-pentopyranosyl) pyrazoles.

✍ Beata Liberek; Zygfryd Smiatacz 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views