1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose | 68733-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6R)-4,6-diacetyloxy-5-azido-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68733-21-1
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: XNCHAEIOCATQMJ-GNIOKVDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  sodium acetate 、 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-((2R,3S,4S)-4-acetoxy-2-acetoxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester 在 sodium azide 、 ammonium cerium(IV) nitrate 、 溶剂黄146 作用下， 生成 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose 、 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose
  参考文献：
  名称：

  Studies on carbohydrates. Part 33: Synthesis of spacer-armed 2-acetamido-2-deoxy-4-O-β-d-galactopyranosyl-α-d-mannosides and their dimers

  摘要：

  The mixture of 3,6-di-O-acetyl-4-0-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-azido-2-deoxy-Dpyranosyl 1-acetates or 1-trichloroacetates and the corresponding mannose type glycosyl donors reacted with the spacer arms di- and triethylene glycol, in dichloromethane solution with BF3. OEt2 and TMSOTf as promoters at room temperature to give highly selective products. Only the mannose type products were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00277-3

文献信息

• Synthesis of 5′-O-(2-Azido-2-deoxy--D-glycosyl)nucleosides and Their Antitumor Activities
  作者：Gui-Sheng Zhang、Jie Chen、Ji-Mei Min、Li-He Zhang

  DOI：10.1002/hlca.200390163

  日期：2003.6

  corresponding α-D-glucopyranose-type glycosyl donor 9/10 reacted at room temperature with protected nucleosides 12–15 in CH2Cl2 solution in the presence of BF3⋅OEt2 as promoter to give 5′-O-(2-azido-2-deoxy-α-D-glycosyl)nucleosides in reasonable yields (Schemes 2 and 3). Only the 5′-O-(α-D-mannopyranosyl)nucleosides were obtained. Compounds 21, 28, 30, and 31 showed growth inhibition of HeLa cells and hepatoma

  1,3,4,6-四-O-乙酰基-2-叠氮基-2-脱氧-β -D-甘露吡喃糖（4）或1,3,6-三-O-乙酰基-2-叠氮基的混合物-2-脱氧-4- ö - （2,3,4,6-四ö乙酰基β -D-吡喃半乳糖基） - β -D-吡喃甘露糖（10）和相应的α -D-吡喃葡萄糖型的糖基供体9 / 10与受保护的核苷在室温下反应12 - 15在CH 2氯2在BF的存在溶液3 ⋅OEt 2作为启动子以合理的产率得到5'- O-（2-叠氮基-2-脱氧-α -D-糖基）核苷（方案2和3）。仅获得5'- O-（α -D-甘露吡喃糖基）核苷。化合物21、28、30和31在体外以10μM的浓度显示出对HeLa细胞和肝癌Bel-7402细胞的生长抑制作用。
• US4195174A
  申请人：——

  公开号：US4195174A

  公开（公告）日：1980-03-25
• US4362720A
  申请人：——

  公开号：US4362720A

  公开（公告）日：1982-12-07