ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-L-glucopyranoside | 932392-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-L-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-3,4-diacetyloxy-6-ethylsulfanyl-5-(prop-2-enoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 932392-85-3
• 化学式: C₁₈H₂₇NO₉S
• 分子量: 433.48
• InChiKey: OSQYKIHNOIARHM-QUSNUVHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-L-glucopyranoside 在 tris-(dibenzylideneacetone)dipalladium(0) N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三苯基膦 、 丙二酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 1,3-bis(undecyloxy)prop-2-yl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-L-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
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-L-glucopyranoside 、 氯甲酸烯丙酯 在 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 反应 4.0h， 以95%的产率得到ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-L-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