✦ LIBER ✦

Synthesis of 1,4-anhydro-2,3,6-tri-O-benzyl-a-d-glucopyranose by cis-ring-closure of a glycosyl chloride

✍ Scribed by Toshihiko Sato; Hiroyuki Nakamura; Yasuo Ohno; Takeshi Endo

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 342 KB
Volume: 199
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)84090-h

No coin nor oath required. For personal study only.

✦ Synopsis

A synthetic approach to 1,4-anhydro-2,3,6-tri-0-benzyl-a-o-glucopyranose by cis-ring closure of a glycosyl chloride has been studied to furnish a starting sugar for the synthesis of a linear (1 -r4)-linked polysaccharide.

Cyclomaltoheptaose was benzylated and the product hydrolyzed to afford 2.3,6-tri-Obenzyl-a-o-glucopyranose, which was converted by HCI-Et,0 into the corresponding glycosyl chloride. Treatment of the latter with NaH in Me,SO gave mainly 2-benzyloxy-3,6-di-O-benzyl-o-glucal, with 1,4-anhydro-2,3,6-tri-0-benzyl-a-D-glucopyranose as a byproduct. However, the 1,4-anhydro sugar could be prepared in good yield by cis ring-closure of 2,3,6-tri-O-benzyl-a-o-glucopyranosyi chloride in a mixture of tetrahydrofuran and sodium hydride.

📜 SIMILAR VOLUMES

Improved synthesis of substituted 2,6-di

Improved synthesis of substituted 2,6-dioxabicyclo[3.1.1]heptanes: 1,3-anhydro-2,4,6-tri-O-benzyl-2,4,6-tri-O-p-bromobenzyl- and -2,4,6-tri-O-p-methylbenzyl-β-d-glucopyranose

✍ Frederick Good; Conrad Schuerch 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 522 KB

Cationic ring-opening polymerization of

Cationic ring-opening polymerization of 1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose as a convenient synthesis of dextran

✍ Toyoji Kakuchi; Atsushi Kusuno; Masakatsu Miura; Harumi Kaga 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 58 KB 👁 1 views

Synthesis and conformation of 1,2-anhydr

Synthesis and conformation of 1,2-anhydro,3,4-6-tri-O-benzyl-β-d-talopyranose

✍ Jianhui Liu; Fanzuo Kong; Lingxiao Cao 📂 Article 📅 1993 🏛 Elsevier Science 🌐 English ⚖ 403 KB

1,2-Anhydro sugar derivatives are important intermediates for the synthesis of oligosaccharides' and polysaccharides2, and also for chemical modification of monosaccharides3. The synthesis of I,2-anhydro-o-manno-4, -o-gluco-5, and -D-galactopyranose6 derivatives by an intramolecular S,2 reaction of

An improved synthesis of 2,3,4-tri-O-ace

An improved synthesis of 2,3,4-tri-O-acetyl-1,6-anhydro-β-d-glucopyranose (levoglucosan triacetate)

✍ Mothe Vaman Rao; Madhavarao Nagarajan 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 197 KB

Improved synthesis of substituted 2,6-di

Improved synthesis of substituted 2,6-dioxabicyclo[3.1.1]heptanes: 1,3-anhydro-2,4,6-tri-O-benzyl- and 1,3-anhydro-2,4,6-tri-O-p-bromobenzyl-β-d-mannopyranose

✍ Fanzuo Kong; Conrad Schuerch 📂 Article 📅 1983 🏛 Elsevier Science 🌐 English ⚖ 504 KB

Synthesis of substituted 2,7-dioxabicycl

Synthesis of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4,6-tri-O-benzyl- and 1,2-anhydro-3,4,6-tri-O-(p-bromobenzyl)-α-d-galactopyranose

✍ Fanzuo Kong; Jingying Du; Heng Shang 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 685 KB