acetyl 2,4-di-O-acetyl-β-D-xylopyranoside | 19186-36-8

• 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: acetyl 2,4-di-O-acetyl-β-D-xylopyranoside
• 英文别名: 1,2,4-tri-O-acetyl-β-D-xylopyranose；[(3R,4S,5R,6S)-5,6-diacetyloxy-4-hydroxyoxan-3-yl] acetate
• CAS: 19186-36-8；71166-82-0；77824-39-6；71143-90-3
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: YTFFSUDKQYXXIY-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  acetyl 2,4-di-O-acetyl-β-D-xylopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 calcium sulfate 、 silver carbonate 、 三氟化硼乙醚 、 氢溴酸 、 乙酸肼 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.67h， 生成 4-(trifluoromethyl)umbelliferyl tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Mechanistic Insights into the 1,3-Xylanases: Useful Enzymes for Manipulation of Algal Biomass

  摘要：

  Xylanases capable of degrading the crystalline microfibrils of 1,3-xylan that reinforce the cell walls of some red and siphonous green algae have not been well studied, yet they could prove to be of great utility in algaculture for the production of food and renewable chemical feedstocks. To gain a better mechanistic understanding of these enzymes, a suite of reagents was synthesized and evaluated as substrates and inhibitors of an endo-1,3-xylanase. With these reagents, a retaining mechanism was confirmed for the xylanase, its catalytic nucleophile identified, and the existence of -3 to +2 substratebinding subsites demonstrated. Protein crystal X-ray diffraction methods provided a high resolution structure of a trapped covalent glycosyl enzyme intermediate, indicating that the 1,3-xylanases likely utilize the S-1(3)-> H-4(3)-> C-4(1) conformational itinerary to effect catalysis.

  DOI：

  10.1021/ja211836t
• 作为产物：
  描述：

  acetyl 2,4-di-O-acetyl-α-D-xylopyranoside 在 氢溴酸 、 溶剂黄146 、 硫脲 作用下， 以 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 10.0h， 生成 acetyl 2,4-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  塞拉利昂木二糖合成酶：三邻乙酰基-二木糖和氯丙烯酰胺

  摘要：

  摘要在干燥的吡啶中，于-30°C用乙酸酐对d-木糖进行选择性乙酰化，得到1,2,3-和1,2,4-tri-O-乙酰基-α-d-吡喃木糖，痕量为2,3,4。 -三-O-乙酰基-d-木吡喃糖。在与前述条件不同的条件下，对d-木糖的乙酰化仅在于在加入乙酸酐之前共沸蒸馏过量的吡啶，得到了八种可能的三乙酸酯的混合物。从3,4-二-O-乙酰基-1获得了1,2,3-，1,2,4-和1,3,4-三-O-乙酰基-β-d-吡喃木糖的明确合成， 2-O-（1-乙氧基亚乙基）-α-d-吡喃木糖，其也得到1,3,4-三-O-乙酰基-α-d-吡喃木糖。通过13 C-和1 Hn.mr光谱分别在62.86和250 MHz下分析上述O-乙酰基衍生物和衍生的一氯乙酰基化合物。

  DOI：

  10.1016/s0008-6215(00)80731-4

文献信息

• Synthesis of reducing disaccharides of d-xylopyranose
  作者：Gérard Excoffier、Didier Gagnaire、Jean-Pierre Utille

  DOI：10.1016/0008-6215(84)85331-8

  日期：1984.6

  Abstract Twenty-one derivatives of reducing disaccharides, d -xylopyranosyl-(1→2)-, -(1→3)-, and -(1→4)-α- or -β- d -xylose were synthesized according to the Helferich and Zirner method. Disaccharides having a pyranose reducing unit were prepared by condensation of 2,3,4-tri-O-acetyl-, 2,4-di-O-acetyl-3-O-chloroacetyl-, and 2,3-di-O-acetyl-4-O-chloroacetyl-α- d -xylopyranosyl bromide with tri-O-acetyl-β-

  摘要合成了二十一种还原二糖衍生物，d-吡喃吡喃糖基-（1→2）-，-（1→3）-和-（1→4）-α-或-β-d-木糖。 Helferich和Zirner方法。通过将2,3,4-三-O-乙酰基-，2,4-二-O-乙酰基-3-O-氯乙酰基和2,3-二-O-缩合来制备具有吡喃糖还原单元的二糖。乙酰基-4-O-氯乙酰基-α-d-吡喃木糖基溴化物与三-O-乙酰基-β-d-吡喃木糖衍生物; 其中1,2,4-三-O-乙酰基-3-O-（2,4-二-O-乙酰基-β-d-吡喃吡喃糖基）-β-d-木吡喃糖和1,2,3-三吡喃糖制备了在非还原糖基团中具有游离羟基的-O-乙酰基-4-O-（2,3-二-O-乙酰基-β-d-吡喃木糖基）-β-d-木吡喃糖，用于合成高级-分子量 线性低聚物。容易获得的5-O-氯乙酰基或5-O-乙酰基-1,2-O-异亚丙基-α-d-木呋喃糖的糖基化反应为1，2-O-异亚丙基-3-O-β-d
• Synthesis of a tetrasaccharide related to the triterpenoid saponin Bellisoside isolated from Bellis perennis (compositae)
  作者：Santanu Mandal、Nayan Sharma、Balaram Mukhopadhyay

  DOI：10.1016/j.tetasy.2010.06.032

  日期：2010.9

  A concise synthesis of a tetrasaccharide related to the triterpenoid saponins Bellisoside has been accomplished from commercially available monosaccharides through rational protecting group manipulations and stereoselective glycosylations. For the glycosylation reactions, H2SO4–silica has been successfully used as an alternative to conventional Lewis acids such as TfOH or TMSOTf. The target tetrasaccharide

  已经通过合理的保护基团操作和立体选择性糖基化作用，从市售单糖中完成了与三萜皂苷甜菊苷相关的四糖的简明合成。对于糖基化反应，H 2 SO 4-二氧化硅已成功用作传统路易斯酸（例如TfOH或TMSOTf）的替代物。靶四糖已经以其对-甲氧基苯基糖苷的形式合成，通过对-甲氧基苯基糖苷的选择性脱保护，然后进行三氯乙亚氨酸化学反应，为进一步的糖缀合物形成留有空间。
• Stereocontrolled Elaboration of Natural (−)-Polycavernoside A, a Powerfully Toxic Metabolite of the Red Alga <i>Polycavernosa</i> <i>tsudai</i>
  作者：Leo A. Paquette、Louis Barriault、Dmitri Pissarnitski、Jeffrey N. Johnston

  DOI：10.1021/ja993487o

  日期：2000.2.1

  A stereoselective total synthesis of natural levorotatory polycavemoside A (1) has been achieved. initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. This objective was followed by preparation of the phenylsulfonyl-substituted tetrahydropyran 23 and aldehyde 30. After proper linking of these key compounds, important information had to be garnered on the sequence of steps that would ultimately result in successful access to 1. Although oxidation to generate alpha-diketone 35 and unmasking of the C-13 hydroxyl did give rise efficiently to lactol 36, this functionality did not pave the way for ensuring macrolactonization. When this sequence of steps was reversed, it was indeed possible to arrive at the heavily functionalized precursor 43. However, numerous experiments failed to result in the requisite activation of C-16 for attachment of the trienyl side chain. However, if the E-vinyl iodide was elaborated in advance of alpha-diketone generation, glycosidation, and complete side chain construction, arrival at 1 proceeded without unsurmountable complications to furnish the targeted marine toxin.
• Stepwise synthesis of linear β-d-(1→3)-xylo-oligosaccharides. Preparation of a β,β,β-d-linked tetrasaccharide derivative
  作者：Danielle Dupeyre、Gérard Excoffier、Jean-Pierre Utille

  DOI：10.1016/0008-6215(84)85016-8

  日期：1984.12