1,2,4,6-tetra-O-acetyl-β-D-glucopyranose | 27086-14-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: Vextupcimuqwao-xvixhaijsa-；[(2R,3S,4S,5R,6S)-3,5,6-triacetyloxy-4-hydroxyoxan-2-yl]methyl acetate
• CAS: 27086-14-2
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: VEXTUPCIMUQWAO-XVIXHAIJSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  458.5±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-acetyl-β-D-glucopyranose 在 吡啶 、 2,4,6-三甲基吡啶 、 palladium on activated charcoal 、 氢气 、 silver perchlorate 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙二醇甲醚 为溶剂， 反应 4.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of nigero-oligosaccharides

  摘要：

  Nigerose [alpha-D-Glcp-(1 --> 3)-D-Glcp], nigerotriose, nigerotetraose, and nigeropentaose have been synthesized by chain elongation starting at the reducing end, from the corresponding octa-, undeca-, tetradeca-, and heptadeca-beta-D-acetates, respectively, via thioglycoside-mediated 1,2-cis coupling, using 1,2,4,6-tetra-O-acetyl-beta-D-glucopyranose as the glucosyl acceptor and methyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside, methyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside, and methyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1 --> 3)-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside as the donors.

  DOI：

  10.1016/0008-6215(92)84098-d
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-(2-naphthyl)methyl-β-D-glucopyranose 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Use of 1,2-dichloro 4,5-dicyanoquinone (DDQ) for cleavage of the 2-naphthylmethyl (NAP) group

  摘要：

  The 2-naphthylmethyl (NAP) group is a versatile group for protection of hydroxyl functions. It is stable to 4% TFA in CHCl3, hot 80% HOAc-H2O, SnCl2-AgOTf and HCl-EtOH, but it can readily be removed with DDQ in CH2Cl2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02046-8

文献信息

• Non-peptide peptidomimetics and related cyclic hexapeptides
  申请人：The Trustees of the University of Pennsylvania

  公开号：US05811512A1

  公开（公告）日：1998-09-22

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor.

  提供的化合物与那些结合G蛋白偶联受体的肽具有交叉反应性，以及用于这些化合物的制备和治疗方法。
• Synthese phosphat-verbrückter d-glucose-einheiten als teilstrukturen phosphorylierter stärken
  作者：Monika Franzkowiak、Joachim Thiem、Corinna Demoulin

  DOI：10.1016/0008-6215(86)84003-4

  日期：1986.12

  6→6-, 6→3-, and g→2-phosphate bridged d -glucose derivatives were prepared by use of selectively protected derivatives and application of a modified phosphoric triester procedure. Specific deblocking of the triesters gave the isomeric (di- d -glucose-6)-hydrogenphosphate, (di- d -glucose-3)-hydrogenphosphate, and (di- d -glucose-2)-hydrogenphosphate. The structures were confirmed by 1 H-, 31 P-, and

  通过使用选择性保护的衍生物并应用改良的磷酸三酯程序，制备了6→6​​-，6→3-和g→2-磷酸桥连的d-葡萄糖衍生物。三酯的特定解封闭得到异构体（（di-d-葡萄糖-6）-磷酸氢根，（di-d-葡萄糖-3）-磷酸氢根和（di-d-葡萄糖-2）-磷酸氢根。通过1 H-，31 P-和13 Cn.mr光谱确认了结构，从而可以研究磷桥周围的构象。
• Non-Peptide peptidomimetics
  申请人：The Trustees of the University of Pennsylvania

  公开号：US05552534A1

  公开（公告）日：1996-09-03

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor. The compounds have the general structure: ##STR1## wherein at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4, or R.sub.5 comprises a functional group which is chemically similar to that found in the peptide of interest.

  提供了与肽交叉反应的化合物，例如那些与G蛋白偶联受体结合的肽，以及相应的制备和治疗方法。这些化合物具有一般结构：##STR1##其中至少有一个R.sub.1、R.sub.2、R.sub.3、R.sub.4或R.sub.5包括与感兴趣的肽中发现的化学相似的官能团。
• The Synthesis of Active-Site Directed Inhibitors of Some β-Glucan Hydrolases
  作者：EB Rodriguez、RV Stick

  DOI：10.1071/ch9900665

  日期：——

  The 2,3-epoxypropyl, 3,4-epoxybutyl and 4,5-epoxypentyl β-glycosides of D-glucose, cellobiose and laminaribiose have been prepared. As well, the 4,5-epoxypentyl β-glycosides of cellotriose, laminaritriose and two other trisaccharides have been synthesized. 3,4-Epoxybutyl β-cellobioside has also been prepared with a 14C-label in the cellobiose residue.

  制备出了 D-葡萄糖、纤维生物糖和片状生物糖的 2,3-环氧丙基、3,4-环氧丁基和 4,5-环氧戊基 β-糖苷。此外，还合成了纤维三糖、片状三糖和另外两种三糖的 4,5-环氧戊基 β-糖苷。此外，还制备了 3,4-环氧丁基 β-纤维二糖苷，并在纤维二糖残基中添加了 14C 标记。
• Synthesis of Gold Glyconanoparticles: Possible Probes for the Exploration of Carbohydrate-Mediated Self-Recognition of Marine Sponge Cells
  作者：Adriana�Carvalho� de Souza、Koen�M. Halkes、Johannes�D. Meeldijk、Arie�J. Verkleij、Johannes�F.�G. Vliegenthart、Johannis�P. Kamerling

  DOI：10.1002/ejoc.200400255

  日期：2004.11

  step in marine sponge cell recognition and adhesion operates via a calcium-dependent proteoglycan− proteoglycan interaction. For the marine sponge Microciona prolifera, one of the carbohydrate epitopes involved in the proteoglycan self-recognition is a sulfated disaccharide [GlcpNAc3S(β1−3)Fucp]. Earlier surface plasmon resonance studies have demonstrated that the proteoglycan self-recognition can be

  海洋海绵细胞识别和粘附的第一步是通过钙依赖性蛋白多糖-蛋白多糖相互作用进行的。对于海洋海绵 Microciona prolifera，参与蛋白多糖自我识别的碳水化合物表位之一是硫酸化二糖 [GlcpNAc3S(β1−3)Fucp]。早期的表面等离子体共振研究表明，当通过与牛血清白蛋白结合多价呈现时，可以用合成的 β-D-GlcpNAc-(13)-α-L-Fucp-(1O) 模拟蛋白多糖的自我识别。在这里，直接合成涂有糖苷 β-D-GlcpNAc3S-(13)-α-L-Fucp-(1O)(CH2)3S( )6SH、β-D-GlcpNAc3S-( 13)-β-L-Fucp-(1O)( )3S( )6SH, β-D-GlcpNAc3S-(1O)( )3S( )6SH, α-L-Fucp-(1O)( )3S( )6SH, β-D-Glcp-NAc3S-(13)-α-L