Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

被引：5

作者：

Collet, Charlotte ^{[1
,2
,3
]}

Chretien, Franoise ^{[1
,2
]}

Chapleur, Yves ^{[1
,2
]}

Lamande-Langle, Sandrine ^{[1
,2
]}

机构：

[1] Univ Lorraine, F-54500 Vandoeuvre Les Nancy, France

[2] CNRS, UMR 7565, F-54506 Vandoeuvre Les Nancy, France

[3] Nancyclotep, Plateforme Imagerie Mol, F-54500 Vandoeuvre Les Nancy, France

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

C-branched; diastereoselective; fluoroinositols; inositols; O-alkylated; AMYLOID-BETA PEPTIDE; SCYLLO-INOSITOL; ALZHEIMERS-DISEASE; GLYCOSYL FLUORIDES; AGGREGATION; CHEMISTRY; PHOSPHATIDYLINOSITOL; STEREOISOMERS; BIOSYNTHESIS; ORIENTATION;

D O I：

10.3762/bjoc.12.39

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments.

引用

页码：353 / 361

页数：9

共 31 条

[21] DIASTEREOSELECTIVE SYNTHESIS OF THE BIS(PHOSPHINO ENOLATO)NICKEL(II) COMPLEX CIS-(NI[PH2PCH=C(O)FE(ETA-C5H5)(CO)(PPH3)]2), DERIVED FROM (ETA-C5H5)FE(CO)(PPH3)C(O)CH2PPH2, AND THE CORRESPONDING CRYSTAL-STRUCTURES
BERNO, P
BRAUNSTEIN, P
FLORIANI, C
CHIESIVILLA, A
GUASTINI, C
INORGANIC CHEMISTRY, 1991, 30 (06) : 1407 - 1410
[22] BRANCHED-CHAIN SUGARS .36. A NEW SYNTHESIS OF METHYL 4-O-BENZOYL-3-BENZOYLAMINO-2,3,6-TRIDEOXY-3-C-METHYL-ALPHA-L-XYLO-HEXOPYRANOSIDE, A DERIVATIVE OF THE BRANCHED-CHAIN AMINO SUGAR OF ANTIBIOTIC A35512B
YASUMORI, T
SATO, K
HASHIMOTO, H
YOSHIMURA, J
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (09) : 2538 - 2542
[23] BRANCHED-CHAIN SUGARS .26. SYNTHESIS OF 4-C-(1-HYDROXYETHYL) DERIVATIVES FROM BENZYL 2,3-DI-O-BENZYL- AND -2,3-O-METHYLENE-BETA-L-THREO-PENTOPYRANOSID-4-ULOSE, AND THE CORRESPONDING "ALPHA-D-XYLO-HEXOPYRANOSID-4-ULOSES
YOSHIMURA, J
MATSUZAWA, M
CARBOHYDRATE RESEARCH, 1981, 96 (01) : 7 - 20
[24] BRANCHED-CHAIN SUGARS .16. SYNTHESIS OF NEW BRANCHED-CHAIN CYCLITOLS HAVING EPI AND ALLO CONFIGURATION AND MYO CONFIGURATION RESPECTIVELY FROM 3-O-BENZYL-5,6-DIDEOXY-5-[C-(1,3-DITHIAN-2-YL)]-6-NITRO-D-ALLOFURANOSEAND -L-TALOFURANOSE
FUNABASHI, M
KOBAYASHI, K
YOSHIMURA, J
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10): : 1618 - 1621
[25] BRANCHED-CHAIN SUGARS .21. SYNTHESIS OF NEW BRANCHED-CHAIN CYCLITOLS HAVING NEO-CONFIGURATION, MYO-CONFIGURATION, AND CHIRO-CONFIGURATION FROM 3-O-BENZYL-5,6-DIDEOXY-5-C-(1,3-DITHIAN-2-YL)-6-NITRO-D-GALACTOFURANOSE AND L-ALTROFURANOSE
IWAKAWA, M
YOSHIMURA, J
FUNABASHI, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (02) : 496 - 500
[26] BRANCHED-CHAIN SUGARS .14. SYNTHESIS OF NEW BRANCHED-CHAIN CYCLITOLS HAVING MYO-CONFIGURATION OR SCYLLO-CONFIGURATION, AND MUCO-CONFIGURATION FROM 3-O-BENZYL-5,6-DIDEOXY-5-C-(1,3-DITHIAN-2-YL)-6-NITRO-L-IDOFURANOSE AND D-GLUCOFURANOSE
FUNABASHI, M
YOSHIMURA, J
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1425 - 1429
[27] Synthesis of new fluoro derivatives of o-carborane [3-F-7,8-C2B9H11]-, 3,6-F2-1,2-C2B10H10, and [6,6′-F2-3,3′-Co(1,2-C2B9H10)2]-
Shmalko, A. V.
Anufriev, S. A.
Timofeev, S. V.
Sivaev, I. B.
Bregadze, V. I.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (01) : 146 - 152
[28] Synthesis of new fluoro derivatives of o-carborane [3-F-7,8-C2B9H11]−, 3,6-F2-1,2-C2B10H10, and [6,6′-F2-3,3′-Co(1,2-C2B9H10)2]−
A. V. Shmalko
S. A. Anufriev
S. V. Timofeev
I. B. Sivaev
V. I. Bregadze
Russian Chemical Bulletin, 2024, 73 : 146 - 152
[29] Hydrothermal synthesis, crystal structure, and spectroscopic characterization of a new organically templated mixed-anion fluoro-arsenate-phosphate iron(III) compound, (C2H10N2)[Fe2(AsO4)2-x(PO4)xF2(H2O)] (x=0.46)
Bazán, B
Mesa, JL
Pizarro, JL
Arriortua, MI
Rojo, T
MATERIALS RESEARCH BULLETIN, 2003, 38 (07) : 1193 - 1202
[30] Hydrothermal synthesis, crystal structure, and spectroscopic and magnetic properties of a new organically templated mixed-anion fluoro-arsenate-phosphate iron(III) compound, (C6H14N2)[Fe3(HAsO4)1.33(HPO4)0.67(ASO4)0.84(PO4)0.16F4]0.5(H2O)
Bazán, B
Mesa, JL
Pizarro, JL
Lezama, L
Garitaonandia, JS
Arriortua, MI
Rojo, T
SOLID STATE SCIENCES, 2003, 5 (09) : 1291 - 1301

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