3,4,6-三-O-乙酰基-1,2-O-亚乙基吡喃己糖 | 630102-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: 3,4,6-三-O-乙酰基-1,2-O-亚乙基吡喃己糖
• 英文名称: 3,4,6-Tri-O-acetyl-1,2-O-<(R,S)-ethylidene>-β-D-mannopyranose
• 英文别名: 3,4,6-tri-O-acetyl-1,2-O-ethylidene-β-D-mannopyranose；3,4,6-tri-O-acetyl-1,2-ethylidene-β-D-mannopyranoside；3,4,6-Tri-O-acetyl-1,2-O-ethylidene-b-D-mannopyranoside；[(3aS,5R,6R,7S,7aS)-6,7-diacetyloxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 630102-81-7
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: NBWFYJVPTWVPKZ-OUPQFMHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-三-O-乙酰基-1,2-O-亚乙基吡喃己糖 在 甲醇 、 sodium methylate 作用下， 反应 4.0h， 以95%的产率得到1,2-O-ethylidene-(R,S)-β-D-mannopyranose
  参考文献：
  名称：

  DNA模板的肽核酸编码的寡糖的同源和异源二聚化作用，模仿了HIV的碳水化合物表位

  摘要：

  全部受控制：杂交的可编程性已用于生成结构的组合文库，该文库模拟复杂碳水化合物与抗体相互作用的拓扑结构，该抗体显示出针对HIV的广谱活性。这种简单的方法涉及以受控方式将标记有肽核酸的寡糖附着到DNA模板上（请参见示意图）。

  DOI：

  10.1002/anie.200903328
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium tetrahydroborate 、 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到3,4,6-三-O-乙酰基-1,2-O-亚乙基吡喃己糖
  参考文献：
  名称：

  二糖为唾液酸醛缩酶底物：在还原端含有唾液酸的二糖的合成。

  摘要：

  DOI：

  10.1002/anie.200604799

文献信息

• Polymethylhydrosiloxane (PMHS): A Convenient Option for Synthetic Applications of the Iodine/Silane Combined Reagent - Straightforward Entries to 2-Hydroxyglycals and Useful Building-Blocks of Glucuronic Acid and Glucosamine
  作者：Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1002/ejoc.201201084

  日期：2013.1

  Polymethylhydrosiloxane (PMHS) proved to be a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. In addition, the scope of this combined reagent was expanded to the especially fast generation of 2-acetoxyglycals, and the rapid synthesis of useful building-blocks of D-glucuronic

  在大量合成过程中，聚甲基氢硅氧烷 (PMHS) 被证明是三乙基硅烷的实用替代品，这些合成过程需要使用碘/硅烷组合试剂快速生成糖基碘。此外，该组合试剂的范围扩大到特别快速生成 2-乙酰氧基糖醛，以及快速合成 D-葡萄糖醛酸和 D-葡萄糖胺的有用结构单元。所有合成目标都在特别短的时间内通过一锅法或通过实验序列获得，无需费力的中间体色谱纯化。
• Towards α- or β-d-C-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-d-glucopyranosyl bromide with cyanoborohydride
  作者：Jean-Pierre Praly、Azin Salek Ardakani、Isabelle Bruyère、Chrystelle Marie-Luce、Bing Bing Qin

  DOI：10.1016/s0008-6215(02)00052-6

  日期：2002.10

  These conditions led to 2-(α- d -manno-, and galactopyranosyl)-ethylphosphonates in 68 and 76% yields. Similarly, radical addition of acetylated 1-bromo-β- d -glucopyranosyl chloride ( 2 ) to acrylonitrile or diethyl vinylphosphonate afforded mainly intermediate chlorides which, upon radical reduction with excess tri- n -butyltin hydride, afforded the corresponding β anomers (40 and 38%, respectively)

  摘要在催化量的氯化三正丁基锡和过量的氰基硼氢化钠（或四正丁基铵）存在下，将乙酰化的α-d-吡喃葡萄糖基溴化物（1）光诱导自由基加成到丙烯腈或乙烯基膦酸二乙酯中，可以高效制备α-构型的壬腈和2-（α-d-吡喃葡萄糖基）-乙基膦酸酯（产率分别为79％和70％）。这些条件导致产率为68％和76％的2-（α-d-甘露糖基和吡喃并吡喃糖基）-乙基膦酸酯。类似地，将乙酰化的1-溴-β-d-吡喃葡萄糖基氯（2）自由基加成到丙烯腈或乙烯基膦酸二乙酯中，主要得到中间体氯化物，在用过量的三正丁基锡氢化物进行自由基还原后，得到相应的β异构体（40和分别由38％的CC和CH键形成。立体控制依赖于d -glycopyranos-1-yl自由基的α-立体选择性猝灭。我们还发现，在叔丁醇中用过量的NaBH 3 CN进行1的紫外光辐照，可得到1,3,4,6-四-O-乙酰基-2-脱氧-α-d-阿拉伯糖-己吡喃糖（结晶后占65％
• Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH
  作者：Matteo Adinolfi、Alfonso Iadonisi、Alessandra Ravidà、Marialuisa Schiattarella

  DOI：10.1016/j.tetlet.2003.09.022

  日期：2003.10

  Peracetylated sugars can be efficiently converted into the corresponding 1,2-ethylidenes, -orthoesters, and -glycals via the in situ generation of glycosyl iodides promoted by I-2/Et3SiH. The approach is straightforward and avoids isolation of the sensitive iodinated intermediates. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose
  作者：Tomonori Mori、Ken Hatano、Koji Matsuoka、Yasuaki Esumi、Eric J. Toone、Daiyo Terunuma

  DOI：10.1016/j.tet.2005.01.090

  日期：2005.3

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.
• Du, Yuguo; Kong, Fanzuo, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 341 - 352
  作者：Du, Yuguo、Kong, Fanzuo

  DOI：——

  日期：——