3-叠氮-2,3-二脱氧基-1-O-(叔丁基二甲基甲硅烷基)-β-D-阿拉伯-六吡喃糖 | 189454-43-1

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-叠氮-2,3-二脱氧基-1-O-(叔丁基二甲基甲硅烷基)-β-D-阿拉伯-六吡喃糖
• 中文别名: 3-叠氮-2,3-二脱氧-1-O-(叔-丁基二甲基甲硅烷基)-β-D-阿拉伯-六吡喃糖；3-叠氮-2,3-二脱氧基-1-O-(叔丁基二甲基甲硅烷基)-Beta-D-阿拉伯-六吡喃糖；3-叠氮-2,3-二脱氧-1-O-(叔丁基二甲基甲硅烷基)-Β-D-阿拉伯-六吡喃糖；3-叠氮基-23-双脱氧-1-o-(叔丁基二甲基甲硅烷基)-β-D-arabino-己基吡喃糖
• 英文名称: 3-azido-1-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-arabinohexopyranoside
• 英文别名: tert-butyldimethylsilyl 3-azido-2,3-dideoxy-β-D-arabino-hexopyranoside；(2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol
• CAS: 189454-43-1
• 化学式: C₁₂H₂₅N₃O₄Si
• 分子量: 303.434
• InChiKey: CHVQAMOISPQQTA-ZNSHCXBVSA-N

物化性质

• 熔点：
  73-75 °C(lit.)
• 稳定性/保质期：
  常温常压下稳定，避免与水分和强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  29329990
• 储存条件：
  密封储存，存放在阴凉干燥的库房中，并远离水源。通常需要使用惰性气体进行保护。

反应信息

• 作为反应物：
  描述：

  3-叠氮-2,3-二脱氧基-1-O-(叔丁基二甲基甲硅烷基)-β-D-阿拉伯-六吡喃糖 在 palladium on activated charcoal 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 5.08h， 生成 4-O-(3"-aminobenzyloxycarbonyl-2",3"-dideoxy-4",6"-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
  参考文献：
  名称：

  Synthesis and Antitumor Activity of New Glycosides of Epipodophyllotoxin, Analogues of Etoposide, and NK 611

  摘要：

  A series of 3-amino- and 3-alkylamino-2-deoxy-beta-D-ribo- and beta-D-arabino-glycosides of 4'-demethylepipodophyllotaxin have been synthesized by means of an improved trimethylsilyl-iodide procedure for the podophyllotoxin-4'-demethylepipodophyllotoxin conversion, an efficient and high yielding synthesis of silyl glycoside donors of 3-azido-2, 3-dideoxy-beta-D-ribo- and beta-D-arabino-hexopyranoside's and stereoselective glycosylations. In vitro evaluation of cytotoxic effects against murine L1210 leukemia critically demonstrates the essential role played by a 4,6-acetal for biological activity. Among the most cytotoxic compounds, 3-amino-2,3-dideoxy- and 3-N,N-(dimethylamino)-2,3-dideoxy etoposide analogues, 17 and 27-29 are at least as potent as etoposide on the in vivo P388 (iv/ip) murine leukemia models. However, surprisingly enough, none of these compounds inhibits the human DNA topoisomerases I or II or binds to tubulin to prevent its polymerization and microtubule assembly. Therefore, their mechanism of action remains to be cleared up.

  DOI：

  10.1021/jm9800752
• 作为产物：
  描述：

  4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-叠氮-2,3-二脱氧基-1-O-(叔丁基二甲基甲硅烷基)-β-D-阿拉伯-六吡喃糖
  参考文献：
  名称：

  Synthesis and Antitumor Activity of New Glycosides of Epipodophyllotoxin, Analogues of Etoposide, and NK 611

  摘要：

  A series of 3-amino- and 3-alkylamino-2-deoxy-beta-D-ribo- and beta-D-arabino-glycosides of 4'-demethylepipodophyllotaxin have been synthesized by means of an improved trimethylsilyl-iodide procedure for the podophyllotoxin-4'-demethylepipodophyllotoxin conversion, an efficient and high yielding synthesis of silyl glycoside donors of 3-azido-2, 3-dideoxy-beta-D-ribo- and beta-D-arabino-hexopyranoside's and stereoselective glycosylations. In vitro evaluation of cytotoxic effects against murine L1210 leukemia critically demonstrates the essential role played by a 4,6-acetal for biological activity. Among the most cytotoxic compounds, 3-amino-2,3-dideoxy- and 3-N,N-(dimethylamino)-2,3-dideoxy etoposide analogues, 17 and 27-29 are at least as potent as etoposide on the in vivo P388 (iv/ip) murine leukemia models. However, surprisingly enough, none of these compounds inhibits the human DNA topoisomerases I or II or binds to tubulin to prevent its polymerization and microtubule assembly. Therefore, their mechanism of action remains to be cleared up.

  DOI：

  10.1021/jm9800752

文献信息

• Preparation of selectively protected protoescigenin derivatives for synthesis of escin analogs and neoglycoconjugates
  作者：Kamil Jatczak、Mariusz Gruza、Katarzyna Filip、Piotr Cmoch、Grzegorz Grynkiewicz

  DOI：10.2478/s11532-014-0572-9

  日期：2014.12.1

  Protoescigenin, the main aglycone of horse chestnut saponin mixture known as escin, was selected as substrate for exploratory chemistry towards selective protection, followed by propargyl ether formation and subsequent condensation with azido-monosaccharides, to obtain novel triazole linked conjugates of the triterpene.

  Protoescigenin 是七叶树皂苷混合物的主要苷元，被称为七叶皂苷，被选为探索性化学的底物，以进行选择性保护，然后形成炔丙醚，随后与叠氮单糖缩合，以获得三萜的新型三唑连接缀合物。
• Synthesis and Antitumor Activity of New Glycosides of Epipodophyllotoxin, Analogues of Etoposide, and NK 611
  作者：Laurent Daley、Yves Guminski、Pierre Demerseman、Anna Kruczynski、Chantal Etiévant、Thierry Imbert、Bridget T. Hill、Claude Monneret

  DOI：10.1021/jm9800752

  日期：1998.11.1

  A series of 3-amino- and 3-alkylamino-2-deoxy-beta-D-ribo- and beta-D-arabino-glycosides of 4'-demethylepipodophyllotaxin have been synthesized by means of an improved trimethylsilyl-iodide procedure for the podophyllotoxin-4'-demethylepipodophyllotoxin conversion, an efficient and high yielding synthesis of silyl glycoside donors of 3-azido-2, 3-dideoxy-beta-D-ribo- and beta-D-arabino-hexopyranoside's and stereoselective glycosylations. In vitro evaluation of cytotoxic effects against murine L1210 leukemia critically demonstrates the essential role played by a 4,6-acetal for biological activity. Among the most cytotoxic compounds, 3-amino-2,3-dideoxy- and 3-N,N-(dimethylamino)-2,3-dideoxy etoposide analogues, 17 and 27-29 are at least as potent as etoposide on the in vivo P388 (iv/ip) murine leukemia models. However, surprisingly enough, none of these compounds inhibits the human DNA topoisomerases I or II or binds to tubulin to prevent its polymerization and microtubule assembly. Therefore, their mechanism of action remains to be cleared up.