1,2:3,4-di-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-galactopyranose | 406947-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-galactopyranose
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1:2,3:4-di-O-isopropylidene-α-D-galactopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 406947-08-8
• 化学式: C₂₆H₃₈O₁₅
• 分子量: 590.579
• InChiKey: KBXNZSMACDLJNP-QCKUOCEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-galactopyranose 在 高氯酸 作用下， 以 乙腈 为溶剂， 生成 4-pentenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,5-tri-O-acetyl-α-D-galactofuranoside
  参考文献：
  名称：

  Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose

  摘要：

  一系列含有6-O-连接的呋喃半乳糖的二糖和三糖被合成，它们是以甲基糖苷的异头混合物形式，通过硅胶负载的高氯酸作为催化剂。

  DOI：

  10.1055/s-2007-965913
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 在 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 、 甲基三辛基氯化铵 、 copper(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  异头磺酰亚胺的合成及其作为新的糖基供体家族的用途

  摘要：

  我们介绍了一种方便的异头磺酰亚胺合成方法，其作为糖基供体的能力已经用各种亲硫试剂和受体进行了测试。

  DOI：

  10.1002/1099-0690(20021)2002:1<171::aid-ejoc171>3.0.co;2-7

文献信息

• Catalytic Glycosylation with Glycosyl Thioimidate Donors
  作者：Cristina Lucas-Lopez、Niamh Murphy、Xiangming Zhu

  DOI：10.1002/ejoc.200800503

  日期：2008.9

  of glycosyl thioimidates, glycosyl N-phenyl-trifluorothioacetimidates, were prepared from the readily available glycosyl thiols in excellent yields. These imidates exhibited very good donor properties under the action of catalytic amounts of BF3·Et2O, and the corresponding glycosidation products were formed in very good to excellent yields. Thus, the first catalytic glycosylations with glycosyl thioimidate

  一类新的糖基硫代亚氨酸盐，即糖基 N-苯基-三氟硫代乙亚胺酸盐，是从容易获得的糖基硫醇以优异的产率制备的。这些亚胺酯在催化量的BF3·Et2O的作用下表现出非常好的供体性质，并且相应的糖苷化产物以非常好的收率形成。因此，实现了与糖基硫代亚氨酸酯供体的第一次催化糖基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Methyl 1,2-Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n-Pent-4-enyl 1,2-Orthoesters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1002/ejoc.201200089

  日期：2012.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors – upon BF3·Et2O activation in CH2Cl2 – in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective

  吡喃甘露糖衍生的 1,2- 原乙酸甲酯 (R = Me) 和 -苯甲酸酯 (R = Ph) 可以作为糖基供体 - 在 CH2Cl2 中 BF3·Et2O 活化后 - 在与单糖受体的糖基化反应中以良好的收率提供二糖。在该过程中，糖基化优于酸催化重排，导致甲基吡喃甘露糖苷。甲基 1,2-原酸酯也可用于单糖二醇的区域选择性糖基化方案，其中它们显示出良好的区域选择性。
• Towards an unprotected self-activating glycosyl donor system: Bromobutyl glycosides
  作者：Benjamin G Davis、Steven D Wood、Michael AT Maughan

  DOI：10.1139/v02-029

  日期：2002.6.1

  Bromobutyl mannopyranosides have been successfully used as both protected and unprotected glycosyl donors both with and without the use of an external activator.Key words: glycosylation, unprotected glycosyl donors, oligosaccharides.

  溴丁基甘露聚糖已成功用作受保护和未受保护的糖基供体，无论是否使用外部活化剂。关键词：糖基化，未受保护的糖基供体，寡糖。
• “One-pot” access to α-<scp>d</scp>-mannopyranosides from glycals employing ruthenium catalysis
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1039/c4ra08241a

  日期：——

  An efficient and convenient one-pot method for the preparation of α-d-mannopyranosides from glycal is described.

  描述了一种从甘露糖环糖制备α-d-甘露聚糖的高效便捷的一锅法方法。
• [bmim][OTf]: a versatile room temperature glycosylation promoter
  作者：M. Carmen Galan、Claire Brunet、Monica Fuensanta

  DOI：10.1016/j.tetlet.2008.11.042

  日期：2009.1

  [bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range of donors and protecting groups. (c) 2008 Elsevier Ltd. All rights reserved.