(3aR,4S,6S,7S,7aR)-7-(benzyloxy)-4-(ethylthio)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran | 132799-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,6S,7S,7aR)-7-(benzyloxy)-4-(ethylthio)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran
• CAS: 132799-02-1
• 化学式: C₁₈H₂₆O₄S
• 分子量: 338.468
• InChiKey: LXKQXTYQZZQWDN-RDDKANTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6S,7S,7aR)-7-(benzyloxy)-4-(ethylthio)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran 在 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 18.25h， 生成 ethyl 2-O-acetyl-4-O-benzyl-α-L-thiorhamnopyranoside
  参考文献：
  名称：

  The synthesis and biological evaluation of mycobacterial p-hydroxybenzoic acid derivatives (p-HBADs)

  摘要：

  合成的对羟基苯甲酸衍生物（p-HBADs）来自结核分枝杆菌，具有抑制宿主免疫反应的能力体外。

  DOI：

  10.1039/c3ob42277a
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.0h， 生成 (3aR,4S,6S,7S,7aR)-7-(benzyloxy)-4-(ethylthio)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  The synthesis and biological evaluation of mycobacterial p-hydroxybenzoic acid derivatives (p-HBADs)

  摘要：

  合成的对羟基苯甲酸衍生物（p-HBADs）来自结核分枝杆菌，具有抑制宿主免疫反应的能力体外。

  DOI：

  10.1039/c3ob42277a

文献信息

• Synthesis of a hexasaccharide repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512
  作者：Pradip Shit、Anup Kumar Misra

  DOI：10.1016/j.carres.2018.12.014

  日期：2019.2

  A convergent synthesis of the hexasaccharide as its 2-aminoethyl glycoside corresponding to the repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512 has been achieved applying a [4 + 2] glycosylation strategy. The disaccharide thioglycoside donor was prepared by combining a d-galactofuranosyl thioglycoside with another l-rhamnosyl thioglycoside acceptor. The

  收敛合成六糖作为其2-氨基乙基糖苷，对应于动物双歧杆菌亚种细胞壁多糖的重复单元。采用[4 + 2]糖基化策略可实现乳酸LKM512。通过将d-半乳糖呋喃糖基硫糖苷与另一种1-鼠李糖基硫糖苷受体结合来制备二糖硫糖苷供体。各个糖基化步骤的产率非常令人满意，并且立体效果优异。六糖中的d-半乳糖呋喃糖基部分的α-糖苷键以非常高的产率获得。
• Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62
  作者：Abhijit Rana、Pradip Shit、Anup Kumar Misra

  DOI：10.1007/s10719-023-10122-x

  日期：2023.8

  A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene

  应用顺序糖基化策略，以非常好的收率实现了亚利桑那沙门氏菌 O62的O特异性多糖的六糖重复单元的直接合成。二羟基化 L-鼠李糖部分的成功区域选择性糖基化允许以最少的合成步骤获得所需的化合物。在六糖衍生物中，TEMPO 催化和[双(乙酰氧基)碘]苯(BAIB) 介导的伯羟基在后期区域选择性氧化成羧酸。糖基化步骤产率高，立体化学结果高。从适当功能化的单糖中间体开始，经过十四个步骤，获得了所需的六糖，总产率为 7%。
• Synthesis and Solution-Phase Conformation of the RG-I Fragment of the Plant Polysaccharide Pectin Reveals a Modification-Modulated Assembly Mechanism
  作者：Eoin M. Scanlan、Mukram M. Mackeen、Mark R. Wormald、Benjamin G. Davis

  DOI：10.1021/ja9090963

  日期：2010.6.2

  The syntheses of pure RG-I fragments of key plant matrix biomolecule pectin using a counterintuitive late-stage convergent cis-glycosylation has allowed detailed analyses of their solution-phase conformations, metal binding affinities, pK(a) values, self-assembly equilibria, and diffusional kinetics. These reveal a striking, right-handed 3(1)-helix that provides an effective and repeating lateral display of putative liganding carboxylates. Moreover, these heteropolymeric structures allow units as short as tetrasaccharides to self-assemble through carbohydrate-carbohydrate interactions that are induced by the presence of Ca(II), a known dynamic trigger in planta. These self-assembly properties can be switched simply by the addition or removal of a single methyl group in this repeating unit through methyl (de)esterification, another known dynamic trigger in planta. Together, the combined effect of Ca(II) and methylation revealed here suggests a concerted molecular basis for these two major dynamic modifications in planta.