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3,7-脱水-1,2-二脱氧-4,5,6,8-四-O-(苯基甲基)-D-甘油型-D-古洛-辛-1-炔糖醇 | 168253-07-4

中文名称
3,7-脱水-1,2-二脱氧-4,5,6,8-四-O-(苯基甲基)-D-甘油型-D-古洛-辛-1-炔糖醇
中文别名
——
英文名称
(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran
英文别名
(2S,2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-ethynyl-tetrahydro-2H-pyran;2,3,4,6-tetra-O-benzyl-1-deoxy-1-ethynyl-β-D-glucopyranose;1-ethynyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose;(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)ethyne;(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)octyne;β-ethynyl 2,3,4,6-tetra-O-benzyl-glucopyranoside;2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne;(2S,3S,4R,5R,6R)-2-ethynyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
3,7-脱水-1,2-二脱氧-4,5,6,8-四-O-(苯基甲基)-D-甘油型-D-古洛-辛-1-炔糖醇化学式
CAS
168253-07-4
化学式
C36H36O5
mdl
——
分子量
548.679
InChiKey
ODYZSGODFGXEDP-LPMXJBPNSA-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):
    5.7
  • 重原子数:
    41
  • 可旋转键数:
    13
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.28
  • 拓扑面积:
    46.2
  • 氢给体数:
    0
  • 氢受体数:
    5

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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

点击查看最新优质反应信息

文献信息

  • Regioselective Synthesis of 6-Alkynyl-6-Deoxy and Pseudo-C-Disaccharides Derivatives of Mannofuranose via a 5,6-Cyclic Sulfate
    作者:Thierry Gourlain、Anne Wadouachi、Daniel Beaupère
    DOI:10.1055/s-1999-3389
    日期:1999.2
    C-6 opening of a 5,6-cyclic sulfate derivative of mannofuranoside 1 with acetylenic anion generated from oct-1-yne or phenylethyne gave corresponding 6-alkynyl-6-deoxy derivatives 2 and 3 respectively. The reaction of 5,6-cyclic sulfate 1 with lithium acetylide derived from monosaccharide led to pseudo-C-disaccharide 5. A one-pot procedure was achieved using lithium acetylide in THF/HMPA, to prepare symmetric pseudo-C-disaccharide 7. This method, used with a 5,6-cyclic sulfate derivative of glucofuranose 11 with the acetylide anion derived from mannofuranose 9, gave the corresponding nonsymmetric pseudo-C-disaccharide 13.
    C-6开环反应:利用从辛-1-炔或苯乙炔生成的炔基负离子,打开甘露呋喃糖苷1的5,6-环硫酸酯生物,分别得到相应的6-炔基-6-脱氧衍生物2和3。5,6-环硫酸酯1与源自单糖炔化物反应,形成伪C-二糖5。通过在THF/HMPA中使用炔化物的一锅法程序,制备了对称伪C-二糖7。该方法应用于葡萄呋喃糖11的5,6-环硫酸酯生物,与源自甘露呋喃糖9的炔化负离子反应,得到相应的非对称伪C-二糖13。
  • Novel Carboranyl C-Glycosides for the Treatment of Cancer by Boron Neutron Capture Therapy
    作者:Lutz F. Tietze、Ulrich Griesbach、Ingrid Schuberth、Ulrich Bothe、Alberto Marra、Alessandro Dondoni
    DOI:10.1002/chem.200390148
    日期:2003.3.17
    The synthesis of the novel unprotected carboranyl C-glycosides 2 and 20-24 starting from ethynyl C-glycosides 1, 5-8, 10, and 13 is described. The new compounds are highly water-soluble and display only a very low cytotoxicity, which makes them promising candidates for use in boron neutron capture therapy for the treatment of cancer.
    描述了从乙炔基C-糖苷1、5-8、10和13开始的新型未保护的碳硼烷基C-糖苷2和20-24的合成。这些新化合物高度溶性,并且仅显示出非常低的细胞毒性,这使其成为有望用于中子俘获疗法以治疗癌症的候选药物。
  • Chemoenzymatic Synthesis of Triazole-Linked Glycopeptides
    作者:Floris Rutjes、Stan Groothuys、Brian Kuijpers、Peter Quaedflieg、Harlof Roelen、Roel Wiertz、Richard Blaauw、Floris van Delft
    DOI:10.1055/s-2006-942509
    日期:——
    Triazole-linked glycopeptides are prepared by C-terminal elongation of glycoamino acids with proteinogenic amino acids following a chemical or enzymatic coupling protocol. Two orthogonal routes for a chemoenzymatic strategy were explored, involving a click-reaction before amide bond formation or in reverse order. It was found that enzymatic peptide coupling under the influence of alcalase proceeds cleanly and in high yields, while the resulting dipeptides can be efficiently clicked to acetylene- or azide-containing sugars.
    三氮唑联接的糖肽通过糖氨基酸的C端延伸,与蛋白质氨基酸按照化学或酶促耦合协议制备。探索了两条正交路径的化学酶促策略,涉及在酰胺键形成之前或顺序相反的点击反应。研究发现,在碱性蛋白酶的影响下,酶促肽耦合过程顺利进行且产率较高,同时所得的二肽可以高效地与含有炔烃叠氮的糖发生点击反应。
  • Facile synthesis of 1,2,3-triazole analogs of SGLT2 inhibitors by ‘click chemistry’
    作者:Lan-Tao Li、Li-Fei Zhou、Yan-Jun Li、Juan Huang、Rui-Hua Liu、Bin Wang、Peng Wang
    DOI:10.1016/j.bmcl.2011.10.062
    日期:2012.1
    Novel analogs of SGLT2 inhibitors containing the 1,2,3-triazole motif were designed and synthesized for urinary glucose excretion evaluation. The C-glucosides with triazole aglycone can be easily constructed by click chemistry. Most of the synthesized compounds increased urinary glucose excretion and demonstrated inhibition of glucose transport.
    设计并合成了含有1,2,3-三唑基序的SGLT2抑制剂的新型类似物,用于尿葡萄糖排泄评估。带有三唑糖苷配基的C-葡萄糖苷可以通过点击化学轻松地构建。大多数合成的化合物会增加尿中葡萄糖的排泄,并显示出对葡萄糖转运的抑制作用。
  • Synthesis of New C- and N-β-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase
    作者:Sándor Kun、Éva Bokor、Ádám Sipos、Tibor Docsa、László Somsák
    DOI:10.3390/molecules23030666
    日期:——
    ,2,3-triazoles were prepared by copper catalyzed azide-alkyne cycloadditions between O-perbenzylated or O-peracetylated β-d-glucopyranosyl ethynes and aryl azides. 1-β-d-Gluco-pyranosyl-4-phenyl imidazole was obtained in a glycosylation of 4(5)-phenylimidazole with O-peracetylated α-d-glucopyranosyl bromide. C-β-d-Glucopyranosyl-N-substituted-tetrazoles were synthesized by alkylation/arylation of O-perbenzoylated
    本研究的目的是拓宽糖原磷酸化酶的C-和N-β-d-葡萄糖基唑类抑制剂的结构-活性关系。通过在O-过苄基化或O-过乙酰化的β-d-葡萄糖乙炔与芳基叠氮化物之间进行催化的叠氮化物-炔烃环加成反应,制得1-芳基-4-β-d-葡萄糖-葡萄糖基-1,2,3-三唑。在4-(5)-苯基咪唑与O-过乙酰化的α-d-葡萄糖化物的糖基化反应中获得了1-β-d-葡糖基-喃基-4-苯基咪唑。通过O-过苯甲酰化的5-β-d-葡萄糖基-四唑的烷基化/芳基化反应或由2,6-脱庚糖甲苯磺酰and和槟榔重氮盐合成C-β-d-戊二糖基-N-取代的四唑。将5-取代的四唑通过O-过乙酰化的α-d-葡萄糖化物糖基化,得到N-β-d-葡萄糖基-C取代的四唑。标准脱保护得到测试化合物,其针对兔肌肉糖原磷酸化酶b进行了测定。多数化合物被证明是无活性的,最好的抑制剂是2-β-d-葡萄糖基-5-苯基四唑(IC50
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