methyl 3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside | 20379-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: (2R,3S,4R,6S)-4-azido-2-(hydroxymethyl)-6-methoxyoxan-3-ol
• CAS: 20379-53-7
• 化学式: C₇H₁₃N₃O₄
• 分子量: 203.198
• InChiKey: FLZWXHAJKPSXOG-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 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

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以98%的产率得到methyl 3-amino-2,3-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  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.

  DOI：

  10.1021/jm00121a005
• 作为产物：
  描述：

  methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside 在 甲醇 、 乙酰氯 作用下， 以98%的产率得到methyl 3-azido-2,3-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  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.

  DOI：

  10.1021/jm00121a005

文献信息

• Synthetic access to spacer-linked 3,6-diamino-2,3,6-trideoxy-α-d-glucopyranosides—potential aminoglycoside mimics for the inhibition of the HIV-1 TAR-RNA/Tat-peptide complex
  作者：Thomas Jöge、Martin Jesberger、Patrick Bröker、Andreas Kirschning

  DOI：10.1016/j.carres.2007.05.015

  日期：2007.9

  The synthesis of spacer-linked neoaminoglycoside 5 is described. Key steps of the synthesis are the introduction of nitrogen functionalities at C-3 and C-6 and the olefin cross metathesis of allyl glycoside 16. Although it is known that Grubbs catalysts tolerate nitrogen functionalities, difficulties were encountered in the cross metathesis reaction. Factors that govern this dimerization are the steric

  描述了间隔基连接的新氨基糖苷5的合成。合成的关键步骤是在C-3和C-6处引入氮官能团以及烯丙基糖苷16的烯烃交叉复分解。尽管已知Grubbs催化剂可耐受氮官能团，但在交叉复分解反应中遇到了困难。决定这种二聚作用的因素是催化剂和底物的空间和电子需求。对同二聚体5的初步生物学评估，通过使用基于荧光滴定的方法研究HIV-1 TAR-RNA / TAt-肽复合物的抑制作用，发现抑制作用为5。
• 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。
• Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives
  作者：Laurent Daley、Pierre Roger、Claude Monneret

  DOI：10.1080/07328309708006508

  日期：1997.1.1

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.
• 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.
• Synthesis, X-ray structure and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-α-d-arabino-hexopyranoside
  作者：Aleksandra Dąbrowska、Paweł Dokurno、Antoni Konitz、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(99)00274-8

  日期：1999.1

  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.