pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside | 142269-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
• 英文别名: 4-pentenyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-pent-4-enoxy-5-(prop-2-enoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 142269-92-9
• 化学式: C₂₁H₃₁NO₁₀
• 分子量: 457.478
• InChiKey: KLGOMBIXIMEONM-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 在 吡啶 、 barium dihydroxide 、 iodonium dicollidine perchlorate 、 camphor-10-sulfonic acid 、 水 、 sodium methylate 、 溶剂黄146 、 barium(II) oxide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-α-D-glucopyranose
  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：

  Pent-4-enyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 、 氯甲酸烯丙酯 在 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 反应 6.0h， 以95%的产率得到pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of l-glucosamine donors for 1,2-trans-glycosylation reactions

  摘要：

  Two new L-glucosarnine donors, that is pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta-L-glucopyranoside 16 and ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-l-thio-beta-L-glucopyranoside 21 were prepared in 12 steps from L-arabinose. The reaction pathway uses 3,4,6-tri-O-acetyl-L-glucal 5, and then 3,4,6-tri-O-acetyl-2-deoxy-2-iodO-alpha-L-mannopyranosyl azide 8 as intermediates. The latter, together with donors 16 and 21, were used for preparing L-glucosamine neoglycolipids. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.011