✦ LIBER ✦

Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy

✍ Scribed by Cecile du Mortier; Rosa M. de Lederkremer

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 539 KB
Volume: 139
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)90005-9

No coin nor oath required. For personal study only.

✦ Synopsis

Debenzoylation of 2,4,6-tri-O-benzoyl-3-deoxy-D-arabino-hexono-l,S-lactone (1) followed by heating in vacua and rebenzoylation afforded 2,5,6-tri-o-benzoyl-3-deoxy-D-arubino-hexono-1,Clactone (2). Reduction of 2 with disiamylborane gave 2,5,6-tri-O-benzoyl-3-deoxy-D-arabino-hexofuranose (3) a convenient furanose derivative for the synthesis of glycosides. Acetylation of 3 with acetic anhydride-pyridine afforded l-O-acetyl-2,5,6-tri-O-benzoyl-3-deoxy-cw-D-urubinohexofuranose (4). Compound 4 was converted into methyl 2,4,6-tri-O-benzoyl-3deoxy-a-D-arubino-hexofuranoside

(5) through the bromide obtained by treatment of 4 with bromotrimethylsilane, followed by methanol. Debenzoylation of 5 gave methyl 3-deoxy-a-D-urubino-hexofuranoside (6). All compounds mentioned were obtained crystalline. Conformational studies of 4,5, and 6 were made by 'H-n.m.r. spectroscopy (DAERM method), and the 13C-n.m.r. spectral data are correlated. The structures of compounds 2,4 and 5 were also confirmed by mass spectrometry.

📜 SIMILAR VOLUMES

Structural analysis of 3-deoxy-d-arabino

Structural analysis of 3-deoxy-d-arabino-heptulosonate 7-phosphate by 1H-and natural-abundance 13C-n.m.r. spectroscopy

✍ Craig C. Garner; Klaus M. Herrmann 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 324 KB

Conformational studies of N-acetyl-N-met

Conformational studies of N-acetyl-N-methyl-l-alanine dimethylamide-d6 by n.m.r. spectroscopy

✍ Yukio Imanishi; Kazuya Kugimiya; Toshinobu Higashimura 📂 Article 📅 1975 🏛 Elsevier Science 🌐 English ⚖ 410 KB

N.m.r. studies of some deoxyhexopyranosi

N.m.r. studies of some deoxyhexopyranosides and the X-ray structures of methyl 3,4,6-tri-O-acetyl-2-deoxy-β-d-arabino-hexopyranoside and methyl 4,6-O-benzylidene-3-deoxy-α-d-arabino-hexopyranoside

✍ Elizabeth Lee; Noeleen Melody; Patrick McArdle; Desmond Cunningham 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 454 KB

Both 'H-and 13C-n.m.r. spectroscopy have been employed in structural studies of the 4,6-O-benzylidene-D-aldohexopyranosides and derivatives, including some deoxy sugars . I4 We now report i3C-n.m.r. data (Table I) for the 4,6-O-benzylidene derivatives of methyl 2-deoxy-( 2) 2-deoxy-3-O-methyl-(3),

Conformational analysis of 6-deoxy-6-flu

Conformational analysis of 6-deoxy-6-fluoro-d-glucopyranose, 6-deoxy-6-fluoro-d-galactopyranose, and 4-deoxy-4-fluro-d-glucopyranose in solution by 1H-n.m.r. spectroscopy

✍ Raymond J. Abraham; Eric J. Chambers; Thomas W. Anthony 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 317 KB

Conformation of the (1→3)-β-d-glucan in

Conformation of the (1→3)-β-d-glucan in the sclerotia of Sclerotinia sclerotiorum IFO 9395 assessed by 13C-c.p.-m.a.s. n.m.r. spectroscopy

✍ Naohito Ohno; Hisami Shinohara; Toshiro Yadomae 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 329 KB

Benzo- and indolo-quinolizine derivative

Benzo- and indolo-quinolizine derivatives XI—The configurational and conformational study of 1,2,3,4,4a,6,7,8,9,13b-decahydro-9aH-pyrido[1,2-f]phenanthridine isomers by 270 MHz 1H n.m.r.

✍ G. Van Binst; G. Laus 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 English ⚖ 369 KB

## Abstract The preferred conformations of the four isomers of 1,2,3,4,4a,6,7,8,9,13b‐decahydro‐9a__H__‐pyrido[1,2‐__f__] phenanthridine have been determined by 270 MHz ^1^H n.m.r. and i.r. spectroscopy. N.m.r. assignments are based on the specific chemical shifts of the protons adjacent to the nit