(1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate) | 163982-16-9

• 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: (1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate)
• 英文别名: [(1S,3R,4R,5S,6R)-4,5-bis(2,2-dimethylpropanoyloxy)-2,7-dioxabicyclo[4.1.0]heptan-3-yl]methyl 2,2-dimethylpropanoate
• CAS: 163982-16-9
• 化学式: C₂₁H₃₄O₈
• 分子量: 414.496
• InChiKey: NFYRGRKXRLCACW-UXXRCYHCSA-N

物化性质

• 沸点：
  457.6±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate) 在 3 A molecular sieve 、 Amberlite IRA₄₀₀ (OH^-) 、 silica gel 作用下， 以 甲醇 、 苯 为溶剂， 反应 40.0h， 生成 (-)-trans-Carveol glucoside
  参考文献：
  名称：

  Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose

  摘要：

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10315-x
• 作为产物：
  描述：

  D-葡萄烯糖 在 4-二甲氨基吡啶 、 2,2-dimethyldioxirane 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 72.0h， 生成 (1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose

  摘要：

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10315-x

文献信息

• A concise and practical stereoselective synthesis of ipragliflozin L-proline
  作者：Shuai Ma、Zhenren Liu、Jing Pan、Shunli Zhang、Weicheng Zhou

  DOI：10.3762/bjoc.13.105

  日期：——

  A concise and practical stereoselective synthesis of ipragliflozin L-proline was presented starting from 2-[(5-iodo-2-fluorophenyl)methyl]-1-benzothiophene and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide without catalyst via iodine-lithium-zinc exchange. The overall yield was 52% in three steps and the product purity was excellent. Two key diastereomers were prepared with efficient and direct

  从2-[（5-碘-2-氟苯基）甲基] -1-苯并噻吩和2,3,4,6-四-O-新戊酰基-α-开始，提出了一种简洁实用的伊普拉列净L-脯氨酸立体选择性合成方法。通过碘-锂-锌交换而无需催化剂的D-吡喃葡萄糖基溴化物。三个步骤的总产率为52％，产品纯度极佳。制备了两个关键的非对映异构体，可直接有效地获得α-C-芳基葡萄糖苷。
• [EN] STEREOSELECTIVE SYNTHESIS OF INTERMEDIATES IN THE PREPARATION OF ß-C-ARYLGLUCOSIDES<br/>[FR] SYNTHÈSE STÉRÉOSÉLECTIVE D'INTERMÉDIAIRES DANS LA PRÉPARATION DE SS-C-ARYLGLUCOSIDES
  申请人：LEK PHARMACEUTICALS

  公开号：WO2015177083A1

  公开（公告）日：2015-11-26

  The invention belongs to the fields of pharmaceutical industry, and particularly to an improved stereoselective synthesis of intermediate compounds for the preparation of gliflozins, for example canagliflozin or structurally similar gliflozins. Gliflozins, such as canagliflozin, dapagliflozin, empagliflozin, or ipragliflozin, inhibit the sodium-dependent glucose cotransporter 2 (SGLT2) in the kidney and as such are useful in the treatment of type-2 diabetes.

  这项发明属于制药行业领域，特别是改进的立体选择性合成中间化合物，用于制备格列非嗪，例如坎格列非嗪或结构类似的格列非嗪。格列非嗪，如坎格列非嗪、达格列非嗪、恩帕格列非嗪或依帕格列非嗪，抑制肾脏中的钠依赖型葡萄糖协同转运蛋白2（SGLT2），因此在治疗2型糖尿病中很有用。
• Stereoselective synthesis of intermediates in the preparation of ß-C-arylglucosides
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2947077A1

  公开（公告）日：2015-11-25

  The invention belongs to the fields of pharmaceutical industry, and particularly to an improved stereoselective synthesis of intermediate compounds for the preparation of gliflozins, for example canagliflozin or structurally similar gliflozins. Gliflozins, such as canagliflozin, dapagliflozin, empagliflozin, or ipragliflozin, inhibit the sodium-dependent glucose cotransporter 2 (SGLT2) in the kidney and as such are useful in the treatment of type-2 diabetes.

  该发明属于制药工业领域，特别涉及一种改进的立体选择性合成中间化合物的方法，用于制备格列酮糖类药物，例如卡格列净或结构类似的格列酮糖类药物。格列酮糖类药物，例如卡格列净、达格列净、恩帕格列净或伊普格列净，通过抑制肾脏中的钠依赖性葡萄糖共转运体2（SGLT2）而有助于治疗2型糖尿病。
• α-<i>C</i>-Glycosides <i>via</i> <i>syn</i> Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/<i>n</i>-Dibutyl Ether
  作者：Simon Wagschal、Johan Guilbaud、Pauline Rabet、Vittorio Farina、Sébastien Lemaire

  DOI：10.1021/acs.joc.5b01472

  日期：2015.9.18

  The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 degrees C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different Omicron-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the alpha-anomer of canagliflozin.
• Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose
  作者：Yoh-ichi Matsushita、Kazuhiro Sugamoto、Yoshio Kita、Takanao Matsui

  DOI：10.1016/s0040-4039(97)10315-x

  日期：1997.12

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.