methyl (1S,2S,4R,5R)-2(-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acetate | 910247-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl (1S,2S,4R,5R)-2(-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acetate
• 英文别名: (1S,2S,4R,5R)-(4-hydroxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-acetic acid；methyl 2-[(1S,2S,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]acetate
• CAS: 910247-22-2
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: KADVXEOPDWIXOQ-UGSJSWHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,2S,4R,5R)-2(-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acetate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到3,6-anhydro-2-deoxy-D-gluco-heptono-1,4-lactone
  参考文献：
  名称：

  Accessing tetrahydrofuran-based natural products by microbial Baeyer–Villiger biooxidation

  摘要：

  利用表达来自 Comamonas sp. NCIMB 9872 的环戊酮单加氧酶的重组全细胞，通过立体选择性 BaeyerâVilliger 生物氧化作用获得的杂环内酯，用于正式全合成含有四氢呋喃结构基团的各种天然产物。

  DOI：

  10.1039/b606633j
• 作为产物：
  描述：

  (1S,6S)-3,9-dioxabicyclo[4.2.1]non-7-en-4-one 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 methyl (1S,2S,4R,5R)-2(-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acetate
  参考文献：
  名称：

  Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation

  摘要：

  In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, tratts-kumausyne) and their novel carba analogs by applying different Baeyer-Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.048