Regioselective fluorination in synthesis of deoxyfluoro quercitols from D-(-)-quinic acid

被引：1

作者：

Shih, Tzenge-Lien ^{[1
]}

Liao, Wen-Yu ^{[1
]}

Yen, Wen-Chun ^{[1
]}

机构：

[1] Tamkang Univ, Dept Chem, New Taipei City 25137, Taiwan

来源：

TETRAHEDRON | 2014年 / 70卷 / 51期

关键词：

Deoxyfluoro quercitols; Fluorination; Glycosidase inhibitors; Regioselective fluorination; D-(-)-Quinic acid; ENANTIOSELECTIVE SYNTHESIS; EXPEDITIOUS SYNTHESIS; FACILE SYNTHESIS; ANALOG;

D O I：

10.1016/j.tet.2014.11.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of six new deoxyfluoro querciotls from D-(-)-quinic acid is described. The key steps involve the regioselective fluorination as well as highly stereoselective dihydroxylation. These synthetic deoxyfluoro quercitols are considered as potential glycosidase inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9621 / 9627

页数：7

共 50 条

[41] Stereoselective Esterase from Pseudomonas putida for D-β Acetylthioisobutyric Acid Synthesis
Chen, Chun-Jung
Shaw, Shyh-Yu
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2007, 63 : S134 - S135
[42] CONCISE TOTAL SYNTHESIS OF (-)-ERINAPYRONE B FROM D-(+)-MALIC ACID
Samala, Ramakrishna
Gurram, Venkateshwarlu
Patro, Balaram
Pottabathini, Narender
Mukkanti, K.
SYNTHETIC COMMUNICATIONS, 2014, 44 (04) : 500 - 506
[43] Synthesis of the hexuronic acids IV. The synthesis of d- galacturonic acid from d-galactose
Niemann, C
Link, KP
JOURNAL OF BIOLOGICAL CHEMISTRY, 1934, 104 (01) : 195 - 204
[44] Regioselective synthesis of 19-fluorovitamin D via fluorination of vitamin D-sulfur dioxide adducts
Iwasaki, Y.
Shimizu, M.
Hirosawa, T.
Yamada, S.
Tetrahedron Letters, 37 (37):
[45] ENANTIOSPECIFIC SYNTHESIS OF INOSITOL POLYPHOSPHATES, PHOSPHATIDYLINOSITIDES, AND ANALOGS FROM (-)-QUINIC ACID
FALCK, JR
ABDALI, A
ACS SYMPOSIUM SERIES, 1991, 463 : 145 - 154
[46] Regioselective synthesis of 19-fluorovitamin D via fluorination of vitamin D-sulfur dioxide adducts
Iwasaki, Y
Shimizu, M
Hirosawa, T
Yamada, S
TETRAHEDRON LETTERS, 1996, 37 (37) : 6753 - 6754
[47] cis-decalins from quinic acid:: Toward a synthesis of branimycin
Marchart, Stefan
Mulzer, Johann
Enev, Valentin S.
ORGANIC LETTERS, 2007, 9 (05) : 813 - 816
[48] Convergent synthesis of D-(-)-quinic and shikimic acid-containing dendrimers as potential C-lectin ligands by sulfide ligation of unprotected fragments
Grandjean, C
Rommens, C
Gras-Masse, H
Melnyk, O
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20): : 2967 - 2975
[49] A STEREOSPECIFIC TOTAL SYNTHESIS OF D-(-)-SHIKIMIC ACID
MCCRINDLE, R
OVERTON, KH
RAPHAEL, RA
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR): : 1560 - 1566
[50] ENZYMATIC-SYNTHESIS OF CHLOROGENIC ACID FROM CAFFEOYL COENZYME-A AND QUINIC ACID
STOCKIGT, J
ZENK, MH
FEBS LETTERS, 1974, 42 (02) : 131 - 134

← 1 2 3 4 5 →