4-甲基伞形酮2-叠氮基-2-脱氧-4,6-O-苯基亚甲基-alpha-D-吡喃半乳糖苷 | 1147438-59-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基伞形酮2-叠氮基-2-脱氧-4,6-O-苯基亚甲基-alpha-D-吡喃半乳糖苷
• 英文名称: 4-methylumbelliferyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: (4-MU) 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside；4-Methylumbelliferyl 2-azido-2-deoxy-4,6-O-phenylmethylene-alpha-D-galactopyranoside；7-[[(2S,4aR,6R,7R,8R,8aR)-7-azido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4-methylchromen-2-one
• CAS: 1147438-59-2
• 化学式: C₂₃H₂₁N₃O₇
• 分子量: 451.436
• InChiKey: MYWUUBHOPGUEKN-IYGHGDFISA-N

物化性质

• 熔点：
  199-200°C
• 溶解度：
  可溶于氯仿（少量）、二氯甲烷（少量）、乙酸乙酯（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  、 4-甲基伞形酮2-叠氮基-2-脱氧-4,6-O-苯基亚甲基-alpha-D-吡喃半乳糖苷 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到4-甲基伞形酮2-叠氮基-2-脱氧-3-O-(四-O-乙酰基-beta-D-吡喃半乳糖基)-4,6-O-苯基亚甲基-alpha-D-吡喃半乳糖苷
  参考文献：
  名称：

  A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

  摘要：

  A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.013
• 作为产物：
  描述：

  4-Methylumbelliferyl 2-Azido-2-deoxy-Alpha-D-Galactopyranoside 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以68.0 mg的产率得到4-甲基伞形酮2-叠氮基-2-脱氧-4,6-O-苯基亚甲基-alpha-D-吡喃半乳糖苷
  参考文献：
  名称：

  A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

  摘要：

  A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.013

文献信息

• A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen
  作者：Shih-Sheng Chang、Chun-Cheng Lin、Yaw-Kuen Li、Kwok-Kong Tony Mong

  DOI：10.1016/j.carres.2008.12.013

  日期：2009.3

  A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen. (C) 2008 Elsevier Ltd. All rights reserved.