✦ LIBER ✦

Synthesis of methyl 2-O-allyl-(and 3-O-allyl-) 5-O-benzyl-β-d-ribofuranoside

✍ Scribed by Trupti Desai; Jill Gigg; Roy Gigg

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 764 KB
Volume: 280
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00308-8

No coin nor oath required. For personal study only.

✦ Synopsis

D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-beta-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-beta-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O-(prop-1-enyl)-beta-D-ribofuranoside.

📜 SIMILAR VOLUMES

Synthesis of allyl and benzyl 4-O-(3,6-d

Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside

✍ Jose R. Mariño-Albernas; Vicente Verez-Bencomo; Leandro Gonzalez; Carlos S. Pere 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 803 KB

Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-a-~glucopyranosyl bromide with either ally1 or benxyl2,4-di-0-methyl-cu+rhamnopyranoside in the presence of mercuric cyanide, followed by 0-deacetylation, gave the title oligosaccharides in excellent yields.

Selective 3-O-allylation and 3-O-benzyla

Selective 3-O-allylation and 3-O-benzylation of methyl α-d-manno-, α-l-rhamno- and β-l-fuco-pyranoside

✍ Guangbin Yang; Fanzuo Kong; Shuhua Zhou 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 250 KB

ChemInform Abstract: One-Pot Synthesis o

ChemInform Abstract: One-Pot Synthesis of 1-Allyl- and 1-Allenyl-6-O-acetyl-2,3,4-tri-O- benzyl-α-D-glycosides from Methyl Tetra-O-benzyl-α-D- glycosides.

✍ S.-C. HUNG; C.-C. LIN; C.-H. WONG 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

Synthesis of benzyl O-(3-O-methyl-β-d-ga

Synthesis of benzyl O-(3-O-methyl-β-d-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-α-d-galactopyranoside and benzyl O-(β-d-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-6-O-methyl-α-d-galactopyranoside as specific acceptors for sialyltransferases

✍ Rakesh K. Jain; Conrad F. Piskorz; E.V. Chandrasekaran; Khushi L. Matta 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 304 KB

ChemInform Abstract: Syntheses and React

ChemInform Abstract: Syntheses and Reactions of 5-O-Acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and -β-D-lyxofuranose, 5-O-Acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-Anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose, and 6-O-Acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and -β-D-talopyranose.

✍ Jun Ning; Fanzuo Kong 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 44 KB 👁 2 views

Synthesis of 2,3-O-isopropylidene- and 3

Synthesis of 2,3-O-isopropylidene- and 3-O-benzoyl-2-O-benzyl-2-C-methyl-l-glyceraldehyde

✍ Masanori Yamaura; Tsuneji Suzuki; Yuji Tagami; Hironobu Hashimoto; Juji Yoshimur 📂 Article 📅 1988 🏛 Elsevier Science 🌐 English ⚖ 438 KB

2-C-Methylglyceraldehyde derivatives are among the simplest branchedchain chiral synthons and both the (R)-enantiomer and the (S)-enantiomer 'To whom correspondence should be addressed. \*The temperature reported in ref. 4 must be revised.