2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate | 132470-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate
• 英文别名: ethyl 4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-gluco-oct-3-ulopyranosonate；2,3,4,6-tetra-O-benzyl-1-(ethoxycarbonyl)methyl-α-D-glucopyranose；ethyl 2-[(2S,3R,4S,5R,6R)-2-hydroxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetate
• CAS: 132470-52-1
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: RKTAIJSQIIRFNC-KFHNNOKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate 在 palladium on activated charcoal 氢气 、 三氟乙酸酐 作用下， 以 吡啶 、 乙醇 、 正己烷 、 氯仿 为溶剂， 反应 2.0h， 生成 ethyl 2-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetate
  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：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 二甲基亚砜 、 lithium hexamethyldisilazane 作用下， 以 乙酸酐 为溶剂， 生成 2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate
  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）。
• Synthesis and in vitro biological evaluation of a carbon glycoside analogue of morphine-6-glucuronide
  作者：James M. MacDougall、Xiao-Dong Zhang、Willma E. Polgar、Taline V. Khroyan、Lawrence Toll、John R. Cashman

  DOI：10.1016/j.bmcl.2005.01.072

  日期：2005.3

  Attachment of a glucose moiety to 6-beta-aminomorphine afforded compound 3, where the glucose moiety was linked to the C-6 nitrogen atom by a two-carbon bridge. The synthesis of 3 was accomplished in eight steps from 3-triisopropylsilyl-6-P-aminomorphine and 2,3,4,6-tetra-O-benzyl-D-glucose. The C-glycoside 3 was prepared with the objective of examining a metabolically stable analogue of morphine-6-glucuronide and determining the potency and selectivity of opioid receptor binding. Competition binding assays showed that 3 bound to the mu opioid receptor with a K-i value of 3.5 nM. The C-glycoside 3 exhibited delta/mu and kappa/mu selectivity ratios of 76 and 165, respectively. The synthetic intermediate (i.e., benzyl precursor, compound 11) bound to the mu opioid receptor with a K-i value of 0.5 nM, was less selective for the mu opioid receptor. The [S-35]GTP gamma S assay was used to evaluate the functional properties of compounds 3 and 11. Compound 3 was determined to be a full agonist at the p opioid receptor, whereas compound 11 was found to be a partial agonist. Compound 3 was determined to be very stable in the presence of human liver S9, and rat and monkey liver microsomes: no detectable loss of 3 was observed up to 90 min. Compound 3 was also very stable at pH 2 and pH 7.4, suggesting that 3 possessed properties for sustained duration of action. (c) 2005 Elsevier Ltd. All rights reserved.
• Two ethyl 2-deoxy-α-<scp>D</scp>-hexo-3,7-pyranoso-3-octulosonate derivatives
  作者：Anthony Linden、Xianfeng Li、C. Kuan Lee

  DOI：10.1107/s0108270101014974

  日期：2001.12.15

  In each of the two pyranoid sugars, ethyl 2-deoxy-4,5,6,8-tetra-O-acetyl-alpha -D-gluco-3,7-pyranoso-3-octulosonate, C18H26O12, and ethyl 2-deoxy-4,5,6,8-tetra-O-benzyl-alpha -D-galacto-3,7-pyranoso-3-octulosonate, C38H42O8, the anomeric configuration is alpha. The acetoxymethyl substituent on the hexopyranose ring of the former compound and the ethoxycarbonylmethyl substituents in both sugars all have the gauche-trans conformation, while the benzyloxymethyl substituent of the galactopyranose sugar has the trans-gauche conformation. In each structure, the anomeric hydroxy group forms an intramolecular hydrogen bond with the carbonyl O atom of the ethoxycarbonylmethyl substituent.