ethyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-2-thio-α-D-gluco-hept-2-ulopyranoside | 223582-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-2-thio-α-D-gluco-hept-2-ulopyranoside
• 英文别名: ethyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethoxysulfonyl-2-thio-α-D-glucohept-2-ulopyranoside；ethyl [(2S,3R,4S,5R,6R)-2-ethylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methanesulfonate
• CAS: 223582-35-2
• 化学式: C₃₉H₄₆O₈S₂
• 分子量: 706.921
• InChiKey: JWKRTVBDLFNALX-GFRPZHATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-2-thio-α-D-gluco-hept-2-ulopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-glucohept-2-ulopyranosyl bromide
  参考文献：
  名称：

  1-脱氧-1-乙氧基磺酰基-庚-2-硫吡喃糖基衍生物的糖基化性质研究。唾液酸路易斯X四糖的新型磺酸模拟物的合成

  摘要：

  研究了在不同条件下使用不同受体的1-脱氧-1-乙氧基磺酰基-庚-2-铀吡喃糖的乙硫基，溴基和氯基衍生物的糖基化反应。在所有情况下，产生外切糖和内切糖的消除副反应发生的比例不同。糖基氯供体被用于糖基化三糖受体，以高收率获得了新的唾液酸路易斯X四糖的磺酸模拟物。

  DOI：

  10.1016/j.carres.2011.04.027
• 作为产物：
  描述：

  5-内酯 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ethyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-2-thio-α-D-gluco-hept-2-ulopyranoside
  参考文献：
  名称：

  醛-2-磺酸的磺甲基类似物。合成新的唾液酸化的Lewis X类似物

  摘要：

  通过将甲磺酸乙酯碳负离子加到醛醇内酯中，合成了醛二-2-磺酸的磺甲基衍生物。唾液酸的路易斯X四糖的磺酰化模拟分子已经通过使用新的磺甲基甲基乌磺酸类似物制备。

  DOI：

  10.1016/s0040-4039(99)00522-5

文献信息

• Synthesis of ketopyranosyl glycosides and determination of their anomeric configuration on the basis of the three-bond carbon–proton couplings
  作者：Gábor Májer、Anikó Borbás、Tünde Zita Illyés、László Szilágyi、Attila Csaba Bényei、András Lipták

  DOI：10.1016/j.carres.2007.05.006

  日期：2007.8

  Anomeric pairs of ketopyranosyl glycosides with various substituents at C(alpha), C(beta) and C(gamma) were synthesized from the corresponding thioglycosides, and the influence of the C(alpha)-C(beta)-C(gamma)-H(gamma) torsion angle and substituent effects on the three-bond carbon-proton couplings was studied. The cis coupling constants range from 1 to 2Hz. The trans couplings are generally as small

  由相应的硫代糖苷合成了在Cα，Cβ和Cγ处具有多个取代基的酮基吡喃糖基糖苷对，并研究了Cα-Cβ-Cγ-的影响。研究了H（γ）扭转角和取代基对三键碳-质子耦合的影响。顺式耦合常数范围为1到2Hz。跨耦合通常小至2.3-2.6Hz；反之亦然。然而，对于带有未取代的γ-碳的化合物，测得的反式耦合相对较大（4.8Hz）。与相应的O-糖苷相比，β-位的S-乙基增加了顺式偶联（高达3.2Hz）。
• Sulfonomethyl analogues of aldos-2-ulosonic acids. Synthesis of a new sialyl Lewis X analogue
  作者：Anikó Borbás、Gabriella Szabovik、Zsuzsa Antal、Pál Herczegh、Attila Agócs、András Lipták

  DOI：10.1016/s0040-4039(99)00522-5

  日期：1999.4

  aldos-2-ulosonic acids have been synthesized by addition of the ethyl methanesulfonate carbanion to aldonolactones. A sulfonylated mimic molecule of the sialyl Lewis X tetrasaccharide has been prepared by using a new sulfonomethyl ulosonic acid analogue.

  通过将甲磺酸乙酯碳负离子加到醛醇内酯中，合成了醛二-2-磺酸的磺甲基衍生物。唾液酸的路易斯X四糖的磺酰化模拟分子已经通过使用新的磺甲基甲基乌磺酸类似物制备。
• Replacement of Carbohydrate Sulfates by Sugar C‐Sulfonic Acid Derivatives
  作者：Anikó Borbás、Magdolna Csávás、László Szilágyi、Gábor Májer、András Lipták

  DOI：10.1081/car-120037571

  日期：2004.12.26

  3'-Substituted p-methoxyphenyl beta-lactosides and one of their 3'-epimer were synthesized. The common feature of these compounds is the presence of a strong negative charge at position C-3' in the form of sulfonic acid moieties. The 3',4'-diol derivative of p-methoxyphenyl lactoside was also glycosylated with the thioglycoside of the sulfoulosonic acid. The two-regioisomeric trisaccharides were isolated but their deprotection failed. The aim of the present study was to find carbohydrate ligand(s), which can inhibit the adhesion between Helicobacter pylori and the gastrointestinal epithelial cells.
• Investigation of glycosylating properties of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranosyl derivatives. Synthesis of a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide
  作者：Magdolna Csávás、Gábor Májer、Mihály Herczeg、Judit Remenyik、László Lázár、Attila Mándi、Anikó Borbás、Sándor Antus

  DOI：10.1016/j.carres.2011.04.027

  日期：2011.9

  Glycosylation reactions of the ethylthio, bromo and chloro derivatives of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranose were studied applying different acceptors under different conditions. Elimination side-reactions affording exo- and endoglycals occured in all cases, however, with different proportions. Glycosyl chloride donor was applied to glycosylate a trisaccharide acceptor obtaining a new sulfonic

  研究了在不同条件下使用不同受体的1-脱氧-1-乙氧基磺酰基-庚-2-铀吡喃糖的乙硫基，溴基和氯基衍生物的糖基化反应。在所有情况下，产生外切糖和内切糖的消除副反应发生的比例不同。糖基氯供体被用于糖基化三糖受体，以高收率获得了新的唾液酸路易斯X四糖的磺酸模拟物。
• Sulfonic acid analogues of the sialyl Lewis X tetrasaccharide
  作者：Anikó Borbás、Gabriella Szabovik、Zsuzsa Antal、Krisztina Fehér、Magda Csávás、László Szilágyi、Pál Herczegh、András Lipták

  DOI：10.1016/s0957-4166(99)00564-9

  日期：2000.2

  Sulfonomethyl mimics of 2-ulosonic acids were prepared by addition of the ethyl methanesulfonate carbanion on aldonolactone derivatives, and these were converted into new analogues of the sialyl Lewis X tetrasaccharide. (C) 2000 Elsevier Science Ltd. All rights reserved.