ethyl-(6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate | 302801-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: ethyl-(6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate
• 英文别名: ethyl 3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]propanoate
• CAS: 302801-26-9
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: QLNWSBXAWBHSKI-FYGCWZCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl-(6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到6,7-Dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octapyranuronic acid
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159
• 作为产物：
  描述：

  在 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以92%的产率得到ethyl-(6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate
  参考文献：
  名称：

  6,7-二脱氧-β-d-ido-octopyranuronates的高效立体选择性合成

  摘要：

  使用高度区域选择性和立体选择性的一锅法从 2- O活化的 β- d-半乳糖-吡喃糖醛酸酯合成稀有且具有挑战性的 β- d - ido - octopyranuronate 构型可以成功。NMR显示β- d - ido -octopyranosyl 环主要采用4 C 1椅子构象。

  DOI：

  10.1002/ejoc.202200175

文献信息

• An Olefin Metathesis Route for the Preparation of (1→6)-Linked <i>C</i>-Disaccharide Glycals. A Convergent and Flexible Approach to <i>C</i>-Saccharide Synthesis
  作者：Maarten H. D. Postema、Daniel Calimente、Lei Liu、Tonja L. Behrmann

  DOI：10.1021/jo0005159

  日期：2000.9.1

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
• Highly Efficient and Stereoselective Synthesis of 6,7‐Dideoxy‐β‐ <scp>d‐</scp> <i>ido</i> ‐octopyranuronates
  作者：Saba Homayonia、Chang‐Chun Ling

  DOI：10.1002/ejoc.202200175

  日期：2022.8.26

  Synthesis of the rare and challenging β-d-ido-octopyranuronate configuration can be succeeded using a highly regio- and stereoselective one-pot process from a 2-O-activated β-d-galacto-octopyranuronate ester. The β-d-ido-octopyranosyl ring was revealed to adopt predominantly a 4C1 chair conformation by NMR.

  使用高度区域选择性和立体选择性的一锅法从 2- O活化的 β- d-半乳糖-吡喃糖醛酸酯合成稀有且具有挑战性的 β- d - ido - octopyranuronate 构型可以成功。NMR显示β- d - ido -octopyranosyl 环主要采用4 C 1椅子构象。