2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose | 121363-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose
• 英文别名: 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-D-glucopyranose；prop-2-enyl N-[(1R,2S,3R,4R,5R)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]carbamate
• CAS: 121363-69-7
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: HJQJODXPOUPZAU-JGKVKWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose 在 四氯化钛 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-benzyl-<3,4-di-O-benzyl-1,2-dideoxy-α-D-glucopyrano>-<2,1-d>-2-oxazolidone
  参考文献：
  名称：

  Selective protections on 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-d-glucopyranose

  摘要：

  Regioselective monoacetylation of 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-beta-D-glucopyranose (1) gave a mixture of 3-O-acetyl and 4-O-acetyl derivatives, the structures of which were established by two-dimensional, phase-sensitive NOESY and confirmed by chemical proofs. The benzylation of 1, on the other hand, led to 2-allyloxycarbonylamino-1,6-anhydro-3,4-di- (5) or 2-allyloxycarbonylamino-1,6-anhydro-2 -N-benzyl-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose (10). The regioselective cleavage of 5 with titanium tetrachloride gave the expected 3-O-benzyl derivative, the structure of which was ascertained by chemical proofs; the same reaction performed on 10 led to the opening of the anhydro ring to afford 3-benzyl-[3,4-di-O-benzyl-1,2-dideoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazolidone.

  DOI：

  10.1016/s0008-6215(00)90550-0
• 作为产物：
  描述：

  2-N-Allyloxycarbonyl-2-amino-2-deoxy-6-O-p-toluenesulfonyl-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 以93%的产率得到2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  A Mild Procedure for the Preparation of 1,6-Anhydro-β-D-hexopyranoses and Derivatives

  摘要：

  使用1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）处理6-O-甲苯磺酰基-D-吡喃葡萄糖1，高产率地获得了相应的1,6-脱水-β-D-己吡喃糖2。这种方法同样适用于处理部分乙酰化的糖类甲苯磺酸酯。

  DOI：

  10.1055/s-1989-27192

文献信息

• LAFONT, DOMINIQUE;BOULLANGER, PAUL;CADAS, OLIVIER;DESCOTES, GERARD, SYNTHESIS,(1989) N, C. 191-194
  作者：LAFONT, DOMINIQUE、BOULLANGER, PAUL、CADAS, OLIVIER、DESCOTES, GERARD

  DOI：——

  日期：——
• A Mild Procedure for the Preparation of 1,6-Anhydro-β-D-hexopyranoses and Derivatives
  作者：Dominique Lafont、Paul Boullanger、Olivier Cadas、Gérard Descotes

  DOI：10.1055/s-1989-27192

  日期：——

  Treatment of reducing 6-O-tosyl-D-glycopyranoses 1 with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded the corresponding 1,6-anhydro-ß-D-hexopyranoses 2 in high yields. Reaction was also performed on partly acetylated tosylates of carbohydrates.

  使用1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）处理6-O-甲苯磺酰基-D-吡喃葡萄糖1，高产率地获得了相应的1,6-脱水-β-D-己吡喃糖2。这种方法同样适用于处理部分乙酰化的糖类甲苯磺酸酯。
• Selective protections on 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-d-glucopyranose
  作者：Abderrahime Bouali、Paul Boullanger、Dominique Lafont、Bernard Fenet

  DOI：10.1016/s0008-6215(00)90550-0

  日期：1992.4

  Regioselective monoacetylation of 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-beta-D-glucopyranose (1) gave a mixture of 3-O-acetyl and 4-O-acetyl derivatives, the structures of which were established by two-dimensional, phase-sensitive NOESY and confirmed by chemical proofs. The benzylation of 1, on the other hand, led to 2-allyloxycarbonylamino-1,6-anhydro-3,4-di- (5) or 2-allyloxycarbonylamino-1,6-anhydro-2 -N-benzyl-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose (10). The regioselective cleavage of 5 with titanium tetrachloride gave the expected 3-O-benzyl derivative, the structure of which was ascertained by chemical proofs; the same reaction performed on 10 led to the opening of the anhydro ring to afford 3-benzyl-[3,4-di-O-benzyl-1,2-dideoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazolidone.