Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst

被引：23

作者：

Jyojima, T ^{[1
]}

Miyamoto, N ^{[1
]}

Ogawa, Y ^{[1
]}

Matsumura, S ^{[1
]}

Toshima, K ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

glycosidation; olivose; olivoside; montmorillonite K-10; environmentally benign synthesis;

D O I：

10.1016/S0040-4039(99)00924-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel stereocontrolled glycosidations of 3,4-di-O-protected olivoses and alcohols using a heterogeneous and environmentally benign solid acid, montmorillonite K-10, have been developed. The glycosidations of the 3-O-Ac-4-O-TBS-olivose (4) and various alcohols using montmorillonite K-10 in CH2Cl2 at 25 degrees C exclusively gave the corresponding alpha-olivosides in high yields. On the other hand, the corresponding beta-olivosides were predominately obtained by the glycosidations of the 3-O-TBS-4-O-Ac-olivose (5) and various alcohols under similar conditions. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：5023 / 5026

页数：4

共 50 条

[41] Montmorillonite K-10 as a catalyst in the synthesis of 5, 5-disubstituted hydantoins under ultrasound irradiation
Safari, J.
Javadian, L.
JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (05) : 981 - 987
[42] Montmorillonite K-10 clay as reusable heterogeneous catalyst for the microwave-mediated solventless synthesis of phthalazinetetraones
Habibi, Davood
Mahmoodi, Nosratollah
Marvi, Omid
CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (02) : 81 - 84
[43] Deprotection of tetrahydropyranyl ethers with montmorillonite K-10 clay in methanol
Taniguchi, T
Kadota, K
El-Azab, AS
Ogasawara, K
SYNLETT, 1999, (08) : 1247 - 1248
[44] Efficient preparation of phenol-enriched bio-oil using cobalt-modified montmorillonite K-10 catalyst
Hong, Wenpeng
Zhang, Yu
Song, Jiaxing
Liu, Haipeng
Zhang, Ling
Wang, Hang
Zhang, Yan
Jiang, Haifeng
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2023, 170 (170)
[45] A facile, mild, and environmentally benign procedure for the cleavage of carbon-nitrogen double bonds using KMnO4 in the presence of montmorillonite K-10 under solvent-free conditions
Mohammadpoor-Baltork, I
Khodaei, MM
Hajipour, AR
Aslani, E
MONATSHEFTE FUR CHEMIE, 2003, 134 (04): : 539 - 543
[46] K-10 montmorillonite: An efficient and reusable catalyst for the aerobic C-C bond cleavage of α-substituted ketones
El Younssi, Iman
Rhadfi, Tarik
Atlamsani, Ahmed
Quisefit, Jean-Paul
Herbst, Frederic
Draoui, Khalid
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 363 : 437 - 445
[47] Montmorillonite KSF and montmorillonite K-10 clays as efficient catalysts for the solventless synthesis of bismaleimides and bisphthalimides using microwave irradiation
Habibi, Davood
Marvi, Omid
ARKIVOC, 2006, : 8 - 15
[48] Hydrogen transfer reduction of ketones catalyzed by Fluka K-10 montmorillonite
Dolmazon, D
Aldea, R
Alper, H
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 136 (02) : 147 - 151
[49] An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis
Lee, JM
Tseng, TH
Lee, YJ
SYNTHESIS-STUTTGART, 2001, (15): : 2247 - 2254
[50] STEREOCONTROLLED ROUTE TO 3-AMINO-2,3,6-TRIDEOXY-HEXOPYRANOSES - K-10 MONTMORILLONITE AS A GLYCOSIDATION REAGENT FOR ACOSAMINIDE SYNTHESIS
FLORENT, JC
MONNERET, C
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) : 1171 - 1172

← 1 2 3 4 5 →