2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethoxysulfonyl-D-gluco-hept-1-enitol | 286860-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethoxysulfonyl-D-gluco-hept-1-enitol
• 英文别名: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethylsulfonato-D-gluco-hept-1-enitol；(1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(ethoxysulfonyl)methylidene-D-glucopyranose；2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethoxysulfonyl-α-D-gluco-hept-1-enitol；ethyl (Z)-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ylidene]methanesulfonate
• CAS: 286860-87-5
• 化学式: C₃₇H₄₀O₈S
• 分子量: 644.786
• InChiKey: VVNJVBLIYJEPKR-FOBPJJCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethoxysulfonyl-D-gluco-hept-1-enitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 正己烷 、 氯仿 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  轻松合成共轭外糖

  摘要：

  探索了两种用于合成各种缀合的外糖的有效方法：（i）通过亲核加糖内酯并随后进行脱水，以及（ii）C-糖苷的硒化并随后去除亚硒氧化物。这些反应以立体选择性方式发生，以仅或主要给出外糖的（Z）-异构体。

  DOI：

  10.1016/s0040-4039(01)01427-7
• 作为产物：
  描述：

  3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-α-D-gluco-hept-2-ulose 在 三氟乙酸酐 作用下， 以 吡啶 为溶剂， 以83%的产率得到2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-ethoxysulfonyl-D-gluco-hept-1-enitol
  参考文献：
  名称：

  轻松合成共轭外糖

  摘要：

  探索了两种用于合成各种缀合的外糖的有效方法：（i）通过亲核加糖内酯并随后进行脱水，以及（ii）C-糖苷的硒化并随后去除亚硒氧化物。这些反应以立体选择性方式发生，以仅或主要给出外糖的（Z）-异构体。

  DOI：

  10.1016/s0040-4039(01)01427-7

文献信息

• Stereochemistry in the Synthesis and Reaction of <i>e</i><i>xo</i>-Glycals
  作者：Wen-Bin Yang、Yu-Ying Yang、Yu-Feng Gu、Shwu-Huey Wang、Che-Chien Chang、Chun-Hung Lin

  DOI：10.1021/jo0255227

  日期：2002.5.1

  Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide

  探索了两种一般方法来立体选择性合成外糖。一种方法利用亲核加成葡萄糖，半乳糖和甘露糖型的完全保护的糖内酯，随后进行脱水，以得到具有（Z）构型的期望的外糖。另一种方法以立体选择性方式进行C-糖苷的硒化。随后的亚硒酸盐消除也提供了（Z）-外糖。制备的葡萄糖型或甘露型的外糖共轭酯与烯丙醇反应，仅得到α-异头物。
• 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.
• 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.