3-butylamido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose | 84730-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-butylamido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 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]butanamide
• CAS: 84730-07-4
• 化学式: C₁₆H₂₇NO₆
• 分子量: 329.393
• InChiKey: UNICVNQPQUARFL-RHZHCTOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-butylamido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以88%的产率得到3,6-N-butylimino-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  用氢化锂铝还原1,2; 5,6-二-O-异亚丙基-α-d-葡糖呋喃糖衍生物; 3,6-亚氨基衍生物的简便合成方法

  摘要：

  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。

  DOI：

  10.1016/0008-6215(83)88284-6
• 作为产物：
  描述：

  丁酰氯 、 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 PS-piperidinomethyl resin 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-butylamido-3-deoxy-1,2;5,6-di-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

• 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.
• 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。