1,2,3,4-di-O-isopropylidene-α-D-galactooct-6-enopyrannuronate d'ethyle | 71553-90-7

• 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: 1,2,3,4-di-O-isopropylidene-α-D-galactooct-6-enopyrannuronate d'ethyle
• 英文别名: ethyl (Z)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octo-6-enopyranuronate；ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate；ethyl (Z)-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]prop-2-enoate
• CAS: 71553-90-7
• 化学式: C₁₆H₂₄O₇
• 分子量: 328.362
• InChiKey: ZXTSQSAEGZSJMS-XKWGVGGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  1,2,3,4-di-O-isopropylidene-α-D-galactooct-6-enopyrannuronate d'ethyle 在 Lindlar's catalyst lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 生成 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：

  双丙酮半乳糖 在 swern reagent 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 4.5h， 生成 1,2,3,4-di-O-isopropylidene-α-D-galactooct-6-enopyrannuronate d'ethyle
  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

文献信息

• Highly regioselective synthesis of glycospiro heterocycles through 1,3-dipolar cycloaddition reaction
  作者：R. Prasanna、S. Purushothaman、R. Raghunathan

  DOI：10.1016/j.tetlet.2010.06.098

  日期：2010.8

  A highly regio-selective synthesis of novel glycospiropyrrolidines has been accomplished by 1,3-dipolar cycloaddition (1,3-DC) reaction. A unique dipolarophile derived from galactose has been reacted with azomethine ylide generated from 1,2-diketones and secondary aminoacids to give the corresponding spiro glycoheterocycles in good yields. The structures were assigned by 2D NMR spectra and the regio-

  通过1，3-偶极环加成（1，3-DC）反应已经完成了新型糖螺吡咯烷的高度区域选择性合成。衍生自半乳糖的独特的双极性亲子试剂已与由1,2-二酮和仲氨基酸生成的偶氮甲碱叶立德反应，以高收率得到相应的螺糖杂环。通过2D NMR光谱确定结构，通过单晶X射线分析确定环加合物的区域和立体化学结果。
• 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。
• Coutrot, Philippe; Grison, Claude; Lecouvey, Marc, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 97, # 1-4, p. 47 - 56
  作者：Coutrot, Philippe、Grison, Claude、Lecouvey, Marc

  DOI：——

  日期：——
• 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.