2,4-O-benzylidene-D-erythritol-1,3-cyclic sulfate | 302579-06-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 2,4-O-benzylidene-D-erythritol-1,3-cyclic sulfate
• 英文别名: (4aS,6R,8aR)-6-phenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3,2]dioxathiine 2,2-dioxide
• CAS: 302579-06-2
• 化学式: C₁₁H₁₂O₆S
• 分子量: 272.279
• InChiKey: MYYGSAXHODZOSI-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-3,4,5-三(苄氧基)-2-[(苄氧基)甲基]哌啶 、 2,4-O-benzylidene-D-erythritol-1,3-cyclic sulfate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以65%的产率得到2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-[[N-(2R,3R)-2,4-O-benzylidene-2,4-dihydroxy-3-(sulfooxy)butyl]iminoonium]-D-glucitol
  参考文献：
  名称：

  烷基化脱氧野尻霉素和 1,5-Dideoxy-1,5-亚氨基木糖醇类似物的合成：极性侧链修饰、锍和硒杂原子变体、构象分析和作为糖苷酶抑制剂的评估

  摘要：

  报道了 N-烷基化脱氧野尻霉素和具有 D-或 L-赤藓糖醇-3-硫酸酯官能化 N-取代基的 1,5-dideoxy-1,5-亚氨基木糖醇衍生物的合成。所用的烷基化剂是环状硫酸盐衍生物，由此选择性地攻击受阻最小的一级中心处的氮原子，得到所需的铵盐。在水溶液中，这些盐在铵中心的构型不稳定。铵盐的锍和/或硒鎓类似物通过类似反应制备。硫属元素盐是作为非对映异构体的混合物获得的，在某些情况下是可分离的，仅在构型稳定的硫或硒原子的立体化学上有所不同。通过详细的 NMR 实验获得了每种化合物的构型和构象的证据。这些化合物是 salacinol 的六元环类似物，是一种已知的锍盐葡萄糖苷酶抑制剂。对目标化合物对葡糖苷酶葡糖淀粉酶 G2 的酶抑制作用的评估表明，这些化合物要么是无活性的，要么最多只是麦芽糖水解的弱抑制剂。

  DOI：

  10.1021/ja0482076
• 作为产物：
  描述：

  (2R,4S,5R)-2-phenyl-5-hydroxy-1,3-dioxane-4-methanol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2,4-O-benzylidene-D-erythritol-1,3-cyclic sulfate
  参考文献：
  名称：

  一类新的糖苷酶抑制剂：沙拉丁醇及其立体异构体的合成。

  摘要：

  Salacinol（4）是Salacia reticulata水提取物中的活性成分之一，传统上在斯里兰卡和印度用于治疗糖尿病。描述了水杨醇（4），水杨醇的对映体（5）和非对映体（7）的合成。合成策略依赖于2,3,5-三-O-苄基-1,4-脱水-4-硫代-D-或L-阿拉伯糖醇在C-1的2,4-O-亚苄基上的选择性亲核攻击D-或L-赤藓糖醇-1,3-环硫酸盐。这项工作旨在解决关于柳氮醇的确切结构的歧义，并最终确定天然产物的结构。

  DOI：

  10.1021/jo001444g

文献信息

• Synthesis of new analogues of salacinol containing a pendant hydroxymethyl group as potential glycosidase inhibitors
  作者：Ravindranath Nasi、B. Mario Pinto

  DOI：10.1016/j.carres.2006.06.022

  日期：2006.10

  The synthesis of new analogues of the naturally occurring glycosidase inhibitor, salacinol, and its ammonium analogue, ghavamiol is described. These analogues contain an additional hydroxymethyl group at C-1, which was intended to form additional polar contacts within the active site of glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least

  描述了天然存在的糖苷酶抑制剂新的类似物salacinol及其铵类似物ghavamiol的合成。这些类似物在C-1处包含一个额外的羟甲基，旨在在糖苷酶的活性位点内形成额外的极性接触。目标两性离子化合物是通过亲核攻击在2,4-O-亚苄基-1-（或d）-赤藓糖醇1,3-环硫酸盐的受阻最少的碳原子上由2,5-脱水-1,3合成的： 4,6-二-O-亚苄基-2,5-二脱氧-5-硫代（或1,5-亚氨基）-1-ID醇。
• Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
  作者：Genzoh Tanabe、Kazuya Yoshikai、Takanori Hatanaka、Mizuho Yamamoto、Ying Shao、Toshie Minematsu、Osamu Muraoka、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2006.10.014

  日期：2007.6.1

  De-O-sulfonated analogs (10a, Y(-)=CH(3)OSO(3) and 10b, Y(-)=Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y(-)=CH(3)OSO(3)) with L-thiosugar moiety (1,4-dideoxy-1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol

  天然存在的糖苷酶抑制剂salacinol的De-O-磺化类似物（10a，Y（-）= CH（3）OSO（3）和10b，Y（-）= Cl）及其非对映异构体（12a，Y（-制备具有L-硫糖基部分（1,4-二脱氧-1,4-表硫基-L-阿拉伯糖醇）的）= CH（3）OSO（3））。检查了它们对肠道麦芽糖酶和蔗糖酶的抑制活性，并与亲本α-糖苷酶抑制剂salacinol（1a）进行了比较。化合物10a和10b对两种酶均显示出与1a相同的有效抑制活性，尽管12a是对蔗糖酶和麦芽糖酶的弱抑制剂。这些结果表明1a的O-磺酸根阴离子部分对于抑制活性不是必需的。
• Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family
  作者：Fumihiro Ishikawa、Aiko Hirano、Yuuto Yoshimori、Kana Nishida、Shinya Nakamura、Katsuki Takashima、Shinsuke Marumoto、Kiyofumi Ninomiya、Isao Nakanishi、Weijia Xie、Toshio Morikawa、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1039/d0ra10038b

  日期：——

  31 family. Salacinol and its 3′-O-benzylated analogs inhibit human lysosomal α-glucosidase at submicromolar levels. Simple structure-activity relationship studies reveal that the salacinol side-chain stereochemistry significantly influences binding to GH31 α-glucosidases.

  我们表明，salacinol 型 α-葡萄糖苷酶抑制剂与 GH 31 家族配体相容。Salacinol 及其 3' - O-苄基化类似物以亚微摩尔水平抑制人溶酶体 α-葡萄糖苷酶。简单的构效关系研究表明，salacinol 侧链立体化学显着影响与 GH31 α-葡萄糖苷酶的结合。
• Synthesis of salacinol
  作者：Hideya Yuasa、Jun Takada、Hironobu Hashimoto

  DOI：10.1016/s0040-4039(00)01129-1

  日期：2000.8

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase
  作者：Ahmad Ghavami、Joan Jo-wen Chen、B. Mario Pinto

  DOI：10.1016/j.carres.2003.09.036

  日期：2004.1

  Two sulfonium salts of 1,4-anhydro-4-thio-D-galactitol, with structures related to the known sulfonium salt glycosidase inhibitor, salacinol, have been synthesized as potential inhibitors of UDP-galactopyranose mutase. The synthetic strategy relies on the alkylation reaction of 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thin-D-galactitol at the sulfur atom with 2,4-O-benzylidene-D- or -L-erythritol-1,3-cyclic sulfate. In each case, the reaction proceeded stereoselectively to yield only one stereoisomer at the stereogenic sulfur atom. The effect of the polar solvent, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), in promoting high-yielding reactions is highlighted. The target compounds are then obtained by hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.