3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 14166-54-2

• 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-O-isopropylidene-α-D-glucofuranose
• 英文别名: N-[(3aR,5S,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetamide
• CAS: 14166-54-2
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: BOUGSMZEXVIRCG-JDDHQFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 platinum on activated charcoal 氧气 作用下， 以 水 为溶剂， 反应 20.0h， 以6%的产率得到3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactam
  参考文献：
  名称：

  Preparation of lactams and lactones using pyridinium dichromate

  摘要：

  DOI：

  10.1016/s0008-6215(00)82594-x
• 作为产物：
  描述：

  3-acetamido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 水 、 溶剂黄146 作用下， 生成 3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2008.05.001

文献信息

• Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide
  作者：Kwan Soo Kim、In Haeng Cho、Byung Ki Yoo、Yang Heon Song、Chi Sun Hahn

  DOI：10.1039/c39840000762

  日期：——

  Di-isopropyl sulphide in combination with N-chlorosuccinimide at 0 ° oxidizes primary alcohols to aldehydes but does not oxidizes secondary alchols, whereas at –78 °C, the same reagent mixture oxidizes secondary alcohols to ketones but does not affect primary alcohols.

  二异丙基硫醚与N-氯代琥珀酰亚胺在0°时结合，将伯醇氧化为醛，但不氧化仲醇，而在–78°C，同一试剂混合物将仲醇氧化为酮，但不影响伯醇。