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Volumn , Issue 5, 2007, Pages 785-789

Synthetic approach to exo-glycals from 1-C-Vinyl-D-glycopyranose derivatives via an SN1′-substitution mechanism

(7) Yamanoi, Takashi a Nara, Yukari a Matsuda, Sho a,b Oda, Yoshiki a Yoshida, Akihiro a Katsuraya, Kaname c Watanabe, Mikio b

a NOGUCHI INSTITUTE (Japan)

b TOKAI UNIVERSITY (Japan)

c WAYO WOMEN'S UNIVERSITY (Japan)

Author keywords

1 C vinyl glycopyranose; exo glycal; SN1 type substitution; Trimethylsilyl trifluoromethanesulfonate

Indexed keywords

1 C VINYL DEXTRO GLYCOPYRANOSE DERIVATIVE; ACETONITRILE; DICHLOROMETHANE; ETHER DERIVATIVE; PYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34047181474 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970751 Document Type: Article

Times cited : (16)

References (17)

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- We also reported the Brønsted acid catalyzed intramolecular β-glycosidation of 1-C-alkyl-D-hexopyranoses to form the anhydroketopyranoses, see: Yamanoi, T.; Matsumura, K.; Matsuda, S.; Oda, Y. Synlett 2005, 2973; see also ref. 1c.
- (d) We also reported the Brønsted acid catalyzed intramolecular β-glycosidation of 1-C-alkyl-D-hexopyranoses to form the anhydroketopyranoses, see: Yamanoi, T.; Matsumura, K.; Matsuda, S.; Oda, Y. Synlett 2005, 2973; see also ref. 1c.

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17
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- Typical Reaction Procedure (see, Table 1, Entry 4) A typical reaction procedure is as follows: to a stirred solution of the allyltrimethylsilane (85.1 μL, 0.54 mmol) and 1 (101.2 mg, 0.18 mmol) was added TMSOTf (6.6 μL, 0.036 mmol) in MeCN-CH2Cl2 (1:1, 3 mL) at -78°C in the presence of dry CaSO4 (ca. 100 mg) in an Ar atmosphere. The resulting mixture was stirred for 2 h. The reaction was then quenched by the addition of a sat. NaHCO3 solution (5 mL, The reaction mixture was extracted with EtOAc, and the organic layer was washed with H2O and a sat. NaCl solution. After the organic layer was dried over anhydrous Na2SO4, the solvent was evaporated under reduced pressure. The crude product was purified by preparative silica gel TLC (EtOAc-hexane, 1:4) to give 4 (61.2 mg, 58, Ketopyranoside 2: [α]D21 +64.4 c 1.12, CHCl3, 1H
- +: 691.3030; found: 691.3077.

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