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octyl 2-O-benzoyl-α-D-arabinofuranoside | 310880-39-8

中文名称
——
中文别名
——
英文名称
octyl 2-O-benzoyl-α-D-arabinofuranoside
英文别名
[(2S,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-octoxyoxolan-3-yl] benzoate
octyl 2-O-benzoyl-α-D-arabinofuranoside化学式
CAS
310880-39-8
化学式
C20H30O6
mdl
——
分子量
366.455
InChiKey
DXRATFJFVTVAEB-XSYGEPLQSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.2
  • 重原子数:
    26
  • 可旋转键数:
    12
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.65
  • 拓扑面积:
    85.2
  • 氢给体数:
    2
  • 氢受体数:
    6

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    —— methyl tri-O-benzoyl-α-D-arabinofuranoside 7473-42-9 C27H24O8 476.483
    —— β-D-arabinofuranose 1,2,5-orthobenzoate 282107-49-7 C12H12O5 236.224
    —— octyl α-D-arabinofranose tetraacetate 352438-36-9 C13H26O5 262.346
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    —— octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside 569659-32-1 C27H34O7 470.563
    —— octyl 3,5-di-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2-O-benzoyl-α-D-arabinofuranoside 676259-70-4 C44H50O14 802.873
    —— octyl 2-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside 310880-58-1 C36H48O6Si 604.859
    —— octyl 3,5-di-O-(2,3-anhydro-α-D-ribofuranosyl)-α-D-arabinofuranoside 676259-73-7 C23H38O11 490.548
    —— octyl 3-O-(2,3-anhydro-α-D-ribofuranosyl)-α-D-arabinofuranoside 676259-72-6 C18H32O8 376.447

反应信息

  • 作为反应物:
    描述:
    octyl 2-O-benzoyl-α-D-arabinofuranosideN-碘代丁二酰亚胺sodium methylatesilver trifluoromethanesulfonate三苯基膦 作用下, 以 四氢呋喃甲醇二氯甲烷 为溶剂, 反应 24.08h, 生成 D-Araf3N(a1-3)[D-Araf3N(a1-5)]D-Araf(a)-O-octyl
    参考文献:
    名称:
    Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues
    摘要:
    The assembly of the arabinan portions of cell wall polysaccharicles in mycobacteria involves a family of arabinosyltransferases (AraT's) that promote the polymerization of decaprenolphosphoarabinose. Mycobacterial viability depends upon the ability of the organism to synthesize an intact arabinan and thus compounds that inhibit these AraT's are both useful biochemical tools as well as potential lead compounds for new anti-tuberculosis agents. We describe here the preparation of oligosaccharide fragments of mycobacterial arabinan that contain arabinofuranosyl residues modified at C-3 by the replacement of the hydroxyl group with an amino, azido or methoxy functionality. Subsequent testing of these oligosaccharides as inhibitors of mycobacterial AraT's revealed that all inhibited the enzymes, but to varying degrees. In further studies, each compound was shown to have only low activity as an inhibitor of mycobacterial growth. (C) 2004 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2004.11.003
  • 作为产物:
    描述:
    methyl tri-O-benzoyl-α-D-arabinofuranoside1,1-二氯甲醚 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium methylate四氯化锡 作用下, 以 甲醇二氯甲烷甲苯 为溶剂, 反应 24.5h, 生成 octyl 2-O-benzoyl-α-D-arabinofuranoside
    参考文献:
    名称:
    Elaboration of Monoarabinofuranosidic Building Blocks
    摘要:
    DOI:
    10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8
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文献信息

  • 2,3-Anhydrosugars in glycoside bond synthesis. Application to the preparation of C-2 functionalized α-d-arabinofuranosides
    作者:Oana M Cociorva、Todd L Lowary
    DOI:10.1016/j.tet.2003.12.022
    日期:2004.2
    novel two-step route has been developed for the synthesis of a panel of oligosaccharides (9–17) containing C-2 functionalized α-d-arabinofuranosyl residues. The first step in this route consists of a highly stereocontrolled glycosylation reaction using a 2,3-anhydrosugar thioglycoside (6). In the second step, the epoxide ring in the 2,3-anhydrosugar glycoside is regioselectively opened at C-2 with sodium
    一种新颖的两步路线已被开发用于寡糖的面板的合成(9 - 17)含C-2官能α-d阿拉伯呋喃糖残基。此路线的第一步是使用2,3-糖苷(6)。在第二步中,用甲醇钠叠氮在C-2上将2,3-糖苷中的环氧化物区域选择性地打开,从而提供具有α-d-阿拉伯呋喃糖基立体化学的产物。对这些靶标的这种方法避免了在具有在C-2处具有非参与基团的阿拉伯呋喃糖基供体的糖基化中固有的潜在的立体控制问题。该路线的收敛性也很高,可在环糖苷27 – 29与亲核试剂反应后制备一系列C-2'和C-2''修饰的寡糖
  • Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases
    作者:Jeongseok Han、Rajendrakumar Reddy Gadikota、Patrick R McCarren、Todd L Lowary
    DOI:10.1016/s0008-6215(02)00541-4
    日期:2003.3
    A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • A comprehensive glycosylation system for the elaboration of oligoarabinofuranosides
    作者:Sylvie Sanchez、Toufiq Bamhaoud、Jacques Prandi
    DOI:10.1016/s0040-4039(00)01273-9
    日期:2000.9
    1,2,5-Orthoesters of D-arabinose are key compounds for the construction of a glycosylation system that allows the stereoselective synthesis of any interglycosidic linkage between arabinofuranosidic units. Application to the synthesis of a pentaarabinofuranoside of the mycobacterial cell wall is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues
    作者:Oana M. Cociorva、Todd L. Lowary
    DOI:10.1016/j.carres.2003.12.015
    日期:2004.3
    The synthesis of a panel of oligosaccharides containing C-5 arabinofuranosyl residues (9-20) is described. These compounds are of interest as potential inhibitors of the alpha-(I --> 5)-arabinosyltransferase involved in the assembly of mycobacterial cell-wall arabinan. In the series of compounds prepared, the 5-OH group on the nonreducing residue(s) is replaced, independently, with an amino, azido. fluoro, or methoxy functionality. The synthesis of the target compounds involved the preparation of a series of C-5 modified arabinofuranosyl thioglycosides (24-26) and their subsequent coupling to the appropriate acceptor species (21-23). Deprotection of the glycosylation products afforded the azido, fluoro, or methoxy analogs directly. The amino derivatives were obtained in one additional step by reduction of the azido compounds. (C) 2004 Elsevier Ltd. All rights reserved.
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