methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside | 20379-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: [(2R,3S,4R,6S)-3-acetyloxy-4-azido-6-methoxyoxan-2-yl]methyl acetate
• CAS: 20379-54-8
• 化学式: C₁₁H₁₇N₃O₆
• 分子量: 287.272
• InChiKey: ZEIDDKDESUEWSM-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranoside 在 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis, X-ray structure and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-α-d-arabino-hexopyranoside

  摘要：

  The synthesis, crystal structure data and 1H and 13C NMR spectroscopy of methyl 3-azido-2,3-dideoxy-alpha-D-arabino-hexopyranoside (5b) is reported. This compound adopts the 4C1 conformation. Hydrogen-bonded molecules of 5b form helices around the crystallographic 4(1) axis.

  DOI：

  10.1016/s0008-6215(99)00274-8

文献信息

• Synthesis, the crystal structure, and high-resolution NMR spectroscopy of methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-α-d-arabino-hexopyranoside
  作者：Aleksandra Dąbrowska、Antoni Konitz、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(01)00302-0

  日期：2002.2

  Selective tosylation followed by acetylation of methyl 3-azido-2,3-dideoxy-alpha-D-arabino-hexopyranoside (1) in pyridine at room temperature affords a mixture of methyl 4-O-acetyl-3-azido-2,3-dideoxy-6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (4) and methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (3). Compound 4 undergoes nucleophilic displacement with

  室温下在甲苯中进行选择性甲苯磺酸化，然后将甲基3-叠氮基-2,3-二脱氧-α-D-阿拉伯糖基己吡喃糖苷（1）乙酰化，得到甲基4-O-乙酰基-3-叠氮基-2,3的混合物-双脱氧-6-二-Op-甲苯基磺酰基-α-D-阿拉伯糖基己吡喃糖苷（4）和甲基3-叠氮基-2,3-二脱氧-4,6-二-Op-甲苯基磺酰基-α-D-阿拉伯糖基己吡喃糖苷（3）。化合物4与碘化钠在乙酸酐中进行亲核取代，得到甲基4-O-乙酰基3-叠氮基2,3,6-三苯氧基-6-碘基-α-D-阿拉伯糖基六吡喃糖苷（7），其晶体结构报道了（1H）和（13）C NMR数据。该化合物采用4C（1）构象。
• Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars
  作者：Pierre Roger、Claude Monneret、Jean Paul Fournier、Patrick Choay、Roselyne Gagnet、Charles Gosse、Yves Letourneux、Ghanem Atassi、Alain Gouyette

  DOI：10.1021/jm00121a005

  日期：1989.1

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.
• The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Marlena Matuszewska、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(02)00288-4

  日期：2002.11

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.