benzyl 3-O-allyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside | 195254-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 3-O-allyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside
• 英文别名: benzyl N-[(2R,4aR,6S,7R,8R,8aS)-2-(2-methoxyphenyl)-6-phenylmethoxy-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 195254-04-7
• 化学式: C₃₂H₃₅NO₈
• 分子量: 561.632
• InChiKey: XOESQNZYBGLEPM-NHMJYFFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-allyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 以21.4%的产率得到1N,1N'-bis-[benzyl 3-O-allyl-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside-2-yl]-1-methylurea
  参考文献：
  名称：

  Unexpected Products in the Lialh₄/Alcl₃-Reduction of 3-O-Substituted and N-Benzyloxycarbonyl-Protected 4,6-O-[2-Methoxybenzylidene]-α-D-Glucosamine Derivatives

  摘要：

  The reductive cleavage of benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-(2-methoxybenzylidene)-alpha-D-glucopyranoside 2 with LiAlH4-AlCl3 gave the corresponding 4-O-(2-methoxybenzyl) ether along with the 6-O-ether as expected. When, however, the 3-hydroxyl group was substituted, acetal cleavage was not the main reaction path. With a 3-O-allyl or a 3-O-methyl group, the unsymmetrical urea derivatives 8 resulted together with the formamido and N-methylamino derivatives 9 and 10, respectively, and no acetal cleavage was observed. Substitution at O-3 with a benzyl group allowed the formation of a small amount of 4-O-ether along with the formamido and N-methylamino derivatives with intact 2-methoxybenzylidene group.

  DOI：

  10.1080/07328309708006541
• 作为产物：
  描述：

  2-甲氧基苯甲醛缩二甲醇 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 85.0 ℃ 、25.0 kPa 条件下， 反应 19.0h， 生成 benzyl 3-O-allyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside
  参考文献：
  名称：

  Unexpected Products in the Lialh₄/Alcl₃-Reduction of 3-O-Substituted and N-Benzyloxycarbonyl-Protected 4,6-O-[2-Methoxybenzylidene]-α-D-Glucosamine Derivatives

  摘要：

  The reductive cleavage of benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-(2-methoxybenzylidene)-alpha-D-glucopyranoside 2 with LiAlH4-AlCl3 gave the corresponding 4-O-(2-methoxybenzyl) ether along with the 6-O-ether as expected. When, however, the 3-hydroxyl group was substituted, acetal cleavage was not the main reaction path. With a 3-O-allyl or a 3-O-methyl group, the unsymmetrical urea derivatives 8 resulted together with the formamido and N-methylamino derivatives 9 and 10, respectively, and no acetal cleavage was observed. Substitution at O-3 with a benzyl group allowed the formation of a small amount of 4-O-ether along with the formamido and N-methylamino derivatives with intact 2-methoxybenzylidene group.

  DOI：

  10.1080/07328309708006541

文献信息

• Unexpected Products in the Lialh₄/Alcl₃-Reduction of 3-<i>O</i>-Substituted and <i>N</i>-Benzyloxycarbonyl-Protected 4,6-<i>O</i>-[2-Methoxybenzylidene]-α-D-Glucosamine Derivatives
  作者：Hans Peter Wessel、Isabelle Plessis、Stéphanie Cassel、Wolf Arnold

  DOI：10.1080/07328309708006541

  日期：1997.8.1

  The reductive cleavage of benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-(2-methoxybenzylidene)-alpha-D-glucopyranoside 2 with LiAlH4-AlCl3 gave the corresponding 4-O-(2-methoxybenzyl) ether along with the 6-O-ether as expected. When, however, the 3-hydroxyl group was substituted, acetal cleavage was not the main reaction path. With a 3-O-allyl or a 3-O-methyl group, the unsymmetrical urea derivatives 8 resulted together with the formamido and N-methylamino derivatives 9 and 10, respectively, and no acetal cleavage was observed. Substitution at O-3 with a benzyl group allowed the formation of a small amount of 4-O-ether along with the formamido and N-methylamino derivatives with intact 2-methoxybenzylidene group.