CAS: 14049-03-7; (2S,3S,4R,5R)-3-Fluoro-2,4,5,6-Tetrahydroxyhexanal

该化合物是主要用于生物化学和医学研究的氟化葡萄糖模拟物,其主要优势在于其结构与甘蔗糖相似,允许其作为代谢探测器,同时防止C-3位置的氟代用造成进一步的酶降解.这种特性使得研究细胞系统中的甘蔗迁移和新陈代谢很有价值,特别是在标有氟-18的正电子排放断层摄影(PET)成像中.该化合物在高代谢组织中的稳定性和选择性吸收增强了其在调查代谢紊乱和癌症研究中的效用.其合成可获取性进一步支持其在机械学研究中的采用.

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29702-43-0 99605-33-1 52904-86-6

欧盟法规

ECHA物质C&L通报

上下游产品

Diacetone D-glucose 3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 1,2,4,6-tetra-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranose 1,2,4,6-tetra-O-acetyl-3-deoxy-3-fluoro-α-D-glucopyranose

合成工艺路线路线简述

    📜1,2:5,6-Di-O-Isopropylidene-3-O-Trifluoromethanesulfonyl-α-D-Allofuranose置于cesium Fluoride体系中,用 1,4-二氧六环,水,叔丁醇 用作溶剂,化学反应 44.0H,反应生成3-氟-3-脱氧-D-吡喃糖
    参考文献:3-Fluoroazetidinecarboxylic Acids And Trans,Trans-3,4-Difluoroproline As Peptide Scaffolds: Inhibition Of Pancreatic Cancer Cell Growth By A Fluoroazetidine Iminosugar
    标题:3-Fluoroazetidinecarboxylic Acids And Trans,Trans-3,4-Difluoroproline As Peptide Scaffolds: Inhibition Of Pancreatic Cancer Cell Growth By A Fluoroazetidine Iminosugar
    摘要:Reverse Aldol Opening Tenders Amides Of 3-Hydroxyazetidinecarboxylic Acids (3-Oh-Aze) Unstable Above Ph 8. Axe,Found In Sugar Beet,Is Mis-Incorporated For Proline In Peptides In Humans And Is Associated With Multiple Sclerosis And Teratogenesis. Axe-Containing Peptides May Be Oxygenated By Prolyl Hydroxylases Resulting In Potential Damage Of The Protein By A Reverse Aldol Of The Hydroxyazetidine; This,Rather Than Changes In Conformation; May Account For The Deleterious Effects Of Axe. This Paper Describes The Synthesis Of 3-Fluoro-Aze Amino Acids As Hydroxy-Aze Analogues Which Are Not Susceptible To Aldol Cleavage. 4-(Azidomethyl)-3-Fluoro-Aze And 3,4-Difluoroproline Are New Peptide Building Blocks. Trans,Trans-2,4-Dihydroxy-3-Fluoroazetidine,An Iminosugar,Inhibits The Growth Of Pancreatic Cancer Cells To A Similar Degree As Gemcitabine.
    Doi:10.1021/acs.Joc.5B00463

    海关参考信息

    专利信息


    专利号:US-8845999-B2
    优先权日:2005-05-23
    标 题 :Tracers for monitoring the activity of sodium/glucose cotransporters in health and disease
    发明人:WRIGHT ERNEST M; BARRIO JORGE R; HIRAYAMA BRUCE A; KEPE VLADIMIR
    权利人:WRIGHT ERNEST M; BARRIO JORGE R; HIRAYAMA BRUCE A; KEPE VLADIMIR; UNIV CALIFORNIA
    摘要:Radiolabeled tracers for sodium/glucose cotransporters (SGLTs), their synthesis, and their use are provided. The tracers are methyl or ethyl pyranosides having an equatorial hydroxyl group at carbon-2 and a C 1 preferred conformation, radiolabeled with 18 F, 123 I, or 124 I, or free hexoses radiolabeled with 18 F, 123 I, or 124 . Also provided are in vivo and in vitro techniques for using these and other tracers as analytical and diagnostic tools to study glucose transport, in health and disease, and to evaluate therapeutic interventions.

    专利号:RU-2193032-C2
    优先权日:1997-07-17
    标 题 :Derivatives of polyhydroxyalkylpyrazines, their synthesis and medicinal agents comprising thereof

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: B A Berkowitz, Et Al. Nondestructive Measurement Of Retinal Glucose Transport And Consumption In Vivo Using Nmr Spectroscopy. J Neurochem. 1995 May;64(5):2325-31.
    [参考文献]: C A Podlasek, Et Al. 19F And 13C Nmr Studies Of Polyol Metabolism In Freeze-Tolerant Pupae Of Hyalophora Cecropia. J Biol Chem. 1994 Jan 28;269(4):2521-8.
    [参考文献]: E L Schwartz, Et Al. Human Primary Visual Cortex Topography Imaged Via Positron Tomography. Brain Res. 1984 Mar 5;294(2):225-30.
    [参考文献]: I L Kwee, Et Al. 31P And 3-Fluoro-3-Deoxy-D-Glucose 19F In Vivo Nmr Spectroscopy Of Aged Rat Brain. Nmr Biomed. 1991 Feb;4(1):38-40.
    [参考文献]: I L Kwee, Et Al. Noninvasive Demonstration Of In Vivo 3-Fluoro-3-Deoxy-D-Glucose Metabolism In Rat Brain By 19F Nuclear Magnetic Resonance Spectroscopy: Suitable Probe For Monitoring Cerebral Aldose Reductase Activities. J Neurochem. 1987 Aug;49(2):428-33.

    合成参考文献


    参考文献:10.1007/bf01115160
    摘要:Agbanyo M, Taylor NF. Incorporation of 3-deoxy-3-fluoro-D-glucose into glycogen and trehalose in fat body and flight muscle in Locusta migratoria. Biosci Rep. 1986 Mar;6(3):309–16. doi: 10.1007/bf01115160.
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