1-O-benzyl-3,4-O-isopropylidene-d-erythritol | 1310460-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzyl-3,4-O-isopropylidene-d-erythritol
• 英文别名: (1S)-2-(benzyloxy)-1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol；(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethanol
• CAS: 1310460-70-8
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: HELOBAGFRJPJDQ-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-3,4-O-isopropylidene-d-erythritol 在 盐酸 、 水 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3,4-anhydro-1-O-benzyl-2-O-(1-tridecyl)-D-erythritol
  参考文献：
  名称：

  Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent alpha-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-D-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used alpha-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.109
• 作为产物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 在 sodium tetrahydroborate 、 二正丁基氧化锡 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.5h， 生成 1-O-benzyl-3,4-O-isopropylidene-d-erythritol
  参考文献：
  名称：

  2,3-二脱氧-2-氟-2,3-内-亚甲基-戊二酸和2,3-二脱氧-2-氟-3- C-羟甲基-2,3-内-亚甲基-戊呋喃糖酶的合成及其应用构型锁定双环核苷的制备

  摘要：

  由d-甘油醛和2,3-二脱氧-2-氟-3- C-羟甲基-2,3-内-亚甲基构筑受保护的2,3-二脱氧-2-氟-2,3-内-亚甲基五呋喃糖酶描述了通过相应的氟代烯丙醇上的Simmons-Smith型立体选择性环丙烷化反应衍生自d-异抗坏血酸的五呋喃糖酶。相应的构象锁定的糖修饰的尿苷和鸟苷核苷的合成是通过Vorbrüggen或Mitsunobu方法实现的。在2D NOESY NMR实验的基础上，对新型核苷进行立体化学确认。2'，3'-二脱氧-2'-氟-3'- C-羟甲基-2'，3'-内含物的分析通过X射线晶体学分析得到-亚甲基-尿苷的主要构象参数，并表明呋喃环采用o E / o T 1，East pucker。在基于丙型肝炎病毒（HCV）细胞的复制子测定中发现尿苷和鸟苷核苷是无活性的，这一点在针对HCV NS5B聚合酶检查相应的三磷酸核苷时得到了证实。

  DOI：

  10.1021/jo502712g

文献信息

• ピラゾール誘導体の製造方法
  申请人：キッセイ薬品工業株式会社

  公开号：JP2018108988A

  公开（公告）日：2018-07-12

  【課題】ピラゾール誘導体の製造方法の提供。【解決手段】式（IIC）、（IID）または（III）で表される化合物と、式（IV）で表される化合物を用いるピラゾール誘導体の製造方法。【選択図】なし

  提供制备嘧啶衍生物的方法。使用式（IIC）、（IID）或（III）表示的化合物和使用式（IV）表示的化合物制备嘧啶衍生物的方法。不包括图。
• PYRAZOLE DERIVATIVE, OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP3315492B1

  公开（公告）日：2020-09-16
• Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’
  作者：Genzoh Tanabe、Weijia Xie、Gorre Balakishan、Mumen F.A. Amer、Nozomi Tsutsui、Haruka Takemura、Shinya Nakamura、Junji Akaki、Kiyofumi Ninomiya、Toshio Morikawa、Isao Nakanishi、Osamu Muraoka

  DOI：10.1016/j.bmc.2016.06.013

  日期：2016.8

  Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3'-O-position in salacinol (1), a highly potent natural alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', were designed and synthesized. In order to verify the computational SAR assessments, their alpha-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a-8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal alpha-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3'-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1. (C) 2016 Elsevier Ltd. All rights reserved.
• EP2671879
  申请人：——

  公开号：——

  公开（公告）日：——
• CYCLIC SULFONIUM SALT, PROCESS FOR PRODUCTION OF SAME, AND alpha-GLUCOSIDASE INHIBITOR COMPRISING SAME
  申请人：Muraoka Osamu

  公开号：US20140031394A1

  公开（公告）日：2014-01-30

  Provided is a novel cyclic sulfonium salt compound which is useful for the prevention or treatment of diabetes and the like. The present invention relates to a novel cyclic sulfonium salt compound represented by general formula (I) or (II), an isomer or solvate of the compound, or a pharmaceutically acceptable salt of the compound or the isomer or solvate. The present invention also relates to an α-glucosidase inhibitor, a pharmaceutical composition for preventing or treating diabetes, and an anti-diabetes food, each of which comprises the compound represented by general formula (I) or (II) and the like.