(E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate | 71553-89-4

• 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: (E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate
• 英文别名: ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate；1,2,3,4-di-O-isopropylidene-α-D-galactooct-6-enopyrannuronate d'ethyle；ethyl (E)-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: 71553-89-4
• 化学式: C₁₆H₂₄O₇
• 分子量: 328.362
• InChiKey: ZXTSQSAEGZSJMS-ZTPVOEKPSA-N

物化性质

• 沸点：
  408.9±45.0 °C(predicted)
• 密度：
  1.175±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  (E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate 在 RuH₂(CO)(PPh₃)₃ 、 双氧水 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Elaboration of Conjugated Alkenes Initiated by Insertion into a Vinylic C-H Bond

  摘要：

  DOI：

  10.1021/ja00124a025
• 作为产物：
  描述：

  双丙酮半乳糖 在 lithium hydroxide 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate
  参考文献：
  名称：

  Diastereoselective Synthesis of Galactopyranosyl Amino Esters and Their Transformation into C‐Nucleosides

  摘要：

  Galactopyranosylated olefinic ester (4) on conjugate addition of amines yielded stereoselectively galactopyranosylated amino esters (5-18) in fair to good yield. The selected amino esters (5, 6, 13, and 15-17) on reaction with isocyanates resulted in ureido galactopyranosyl amino esters (19-24) in very good yields. Lactamization of compounds 19-24 with DBU, 4 Angstrom MS, and tetrabutylammonium bromide in refluxing toluene gave respective C-galactopyranosyl dihydropyrimidine-2,4-diones (25-30) in respectable yields.

  DOI：

  10.1081/car-120030140

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：——
• Tetra-n-butylammonium fluoride: an efficient base for aza-Michael addition—synthesis of glycosyl β-amino acid esters
  作者：G.V.M. Sharma、V.Goverdhan Reddy、A.Subhash Chander、K.Ravinder Reddy

  DOI：10.1016/s0957-4166(02)00047-2

  日期：2002.2

  A mild and efficient route to glycosyl beta-amino acid esters. exploiting the stereoselective Michael addition of benzylamine, in the presence of tetra-n-butylammonium fluoride, to sugar derived gamma-alkoxy alpha,beta-unsaturated esters is described. (C) 2602 Published by Elsevier Science Ltd.
• Diastereoselective Synthesis of Galactopyranosyl Amino Esters and Their Transformation into C‐Nucleosides
  作者：Diksha Katiyar、Ram Chandra Mishra、Rama Pati Tripathi

  DOI：10.1081/car-120030140

  日期：2004.12.26

  Galactopyranosylated olefinic ester (4) on conjugate addition of amines yielded stereoselectively galactopyranosylated amino esters (5-18) in fair to good yield. The selected amino esters (5, 6, 13, and 15-17) on reaction with isocyanates resulted in ureido galactopyranosyl amino esters (19-24) in very good yields. Lactamization of compounds 19-24 with DBU, 4 Angstrom MS, and tetrabutylammonium bromide in refluxing toluene gave respective C-galactopyranosyl dihydropyrimidine-2,4-diones (25-30) in respectable yields.