3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 13964-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 3-acetamido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose；3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose；3-Acetamido-3-deoxy-1,2:5,6-di-O-isopropyliden-α-D-glucofuranose；3-(Acetylamino)-3-deoxy-1,2:5,6-bis-O-(1-methylethylidene)-I+/--D-glucofuranose；N-[(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetamide
• CAS: 13964-24-4
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: ARBXTIYDTCGPSN-IYKVGLELSA-N

物化性质

• 沸点：
  437.1±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 硫酸 作用下， 生成 3-acetamido-3-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  使用酸酐-甲基亚砜混合物和pfitzner-moffatt试剂可氧化某些碳水化合物衍生物。轻松合成3-acetamido-3-deoxy-D-葡萄糖和3-amino-3-deoxy-D-木糖

  摘要：

  提供的实施例进一步证明了Pfitzner-Moffatt试剂和酸酐-甲基亚砜混合物作为碳水化合物化学中的氧化剂的价值。由1,2：5,6-二-O-异亚丙基-α-D-已开发出3-乙酰氨基-3-脱氧-D-葡萄糖和3-氨基-3-脱氧-D-木糖的方便且立体有择的合成方法葡萄糖呋喃糖。

  DOI：

  10.1016/s0008-6215(00)82207-7
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 在 吡啶 、 2(1H)-吡啶硫酮,1-(乙酰氧基)- 、 硼酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Nitrogen transfer to carbon radicals

  摘要：

  DOI：

  10.1021/ja00040a088

文献信息

• Reduction of 1,2;5,6-di-O-isopropylidene-α-d-glucofuranose derivatives with lithium aluminium hydride; a facile syntehtic method for 3,6-imino derivatives
  作者：Masahide Yamada、Kohichi Tachibana、Toshio Kuroda、Tohru Sakakibara

  DOI：10.1016/0008-6215(83)88284-6

  日期：1983.2

  3-acylamido- or alkylimino-3-deoxy-1,2;5,6-di- O -isopropylidene-α- d -glucofuranose with lithium aluminum hydride in boiling 1,4-dioxane afforded unusual products, namely, 3,6- N -alkylimino-3,6-dideoxy-1,2- O -isopropylidene-α- d -glucofuranose or 6- O -isopropyl-1,2- O -isopropylidene-α- d -glucofuranose derivatives. 3,6- N -(Benzyloxy)imino-3,6-dideoxy-1,2- O -isopropylidene-β- l -idofuranose, a

  摘要在沸腾的1,4-二恶烷中用氢化铝锂处理3-酰氨基-或烷基亚氨基-3-脱氧-1,2; 5,6-二-O-异亚丙基-α-d-葡萄糖呋喃糖可得到不同寻常的产物，即3，6-N-烷基亚氨基-3，6-二氧-1,2-O-异亚丙基-α-d-葡糖呋喃糖或6-O-异丙基-1,2-O-异亚丙基-α-d-葡糖呋喃糖衍生物。通过该反应，制备了3，6-N-（苄氧基）亚氨基-3，6-二脱氧-1,2-O-异亚丙基-β-1-异呋喃糖，其是合成茴香霉素的关键中间体。
• Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells
  作者：Martina Landi、Giorgio Catelani、Felicia D'Andrea、Eleonora Ghidini、Gabriele Amari、Puccini Paola、Nicoletta Bianchi、Roberto Gambari

  DOI：10.1016/j.ejmech.2008.05.001

  日期：2009.2

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Szabovik; Medgyes; Antal, Polish Journal of Chemistry, 1999, vol. 73, # 6, p. 1003 - 1009
  作者：Szabovik、Medgyes、Antal、Varga、Knott、Liptak

  DOI：——

  日期：——
• The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
  作者：Derek H. R. Barton、Joseph C. Jaszberenyi、Emmanouil A. Theodorakis、J. H. Reibenspies

  DOI：10.1021/ja00071a017

  日期：1993.9

  A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
• Gurjar, M. K.; Patil, V. J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1017 - 1020
  作者：Gurjar, M. K.、Patil, V. J.

  DOI：——

  日期：——