methyl 3-amino-2,3-dideoxy-β-D-arabino-hexopyranoside | 116724-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-amino-2,3-dideoxy-β-D-arabino-hexopyranoside
• 英文别名: Methyl-<3-Amino-2.3-didesoxy-β-D-arabino-hexopyranosid>；(2R,3S,4R,6R)-4-amino-2-(hydroxymethyl)-6-methoxyoxan-3-ol
• CAS: 116724-60-8
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: FEOSBRNHHYNQSH-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-2,3-dideoxy-β-D-arabino-hexopyranoside 在 sodium nitrite 作用下， 以 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 beta-D-arabino-Hexopyranoside, methyl 3-((((2-chloroethyl)nitrosoamino)carbonyl)amino)-2,3-dideoxy-
  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 palladium on activated charcoal 吡啶 、 甲醇 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 58.0h， 生成 methyl 3-amino-2,3-dideoxy-β-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

• Evaluation of the protolytic equilibria and catalytic activity of sugar-based Schiff base ligands with VO2+ and MoO22+ cations in sulfoxidation and epoxidation reactions
  作者：Katarzyna Madejska、Marta Karman、Grzegorz Romanowski、Agnieszka Chylewska、Aleksandra Dąbrowska

  DOI：10.1016/j.poly.2021.115481

  日期：2021.11

  3-dideoxy-d-arabino-hexopyranosides ten new sugar-modified Schiff base ligands have been synthesized after monocondensation reaction with five o-hydroxyaromatic aldehydes, i.e. salicylaldehyde and its five para-substituted derivatives. The acidity constants and acid-base equilibria processes in polar solution were calculated from data obtained after spectrophotometric titrations at room temperature. The

  基于这两个端基异构的3-氨基-2,3-二脱氧d -阿拉伯-hexopyranosides monocondensation反应后10新糖改性的席夫碱配体已被合成具有五个ö -hydroxyaromatic醛，水杨醛即及其五个对-取代的衍生物。极性溶液中的酸度常数和酸碱平衡过程是根据室温下分光光度法滴定后获得的数据计算得出的。发现第一个酸度常数与烯胺氮的去质子化有关，第二个常数对应于酚氧的去质子化。在光谱 IR、UV-Vis 和 NMR 技术的帮助下，讨论了烯醇-亚胺和酮-烯胺互变异构形式和质子 1,5-重排的贡献。最后，通过将所有合成的糖基席夫碱分别与 VO(acac) 2或 MoO 2 (acac) 2混合，原位生成催化剂，并且已经在使用叔丁基过氧化氢 (TBHP) 作为末端氧化剂的苯硫醚不对称亚砜氧化和苯乙烯、环己烯和S (-)-柠檬烯的环氧化中进行了测试。
• 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.
• Crystal structure of methyl 3-amino-2,3-dideoxy-β-d-arabino-hexopyranoside. Stabilization of the crystal lattice by a double network of N–H⋯O, O–H⋯N and O–H⋯O interactions
  作者：Aleksandra Dąbrowska、Dagmara Jacewicz、Artur Sikorski、Lech Chmurzyński

  DOI：10.1016/j.carres.2005.06.031

  日期：2005.9

  The structure, conformation and configuration of methyl 3-amino-2,3-dideoxy-beta-D-arabino-hexopyranoside were investigated by H-1 NMR, C-13 NMR and IR spectroscopy, as well as by optical rotation. The crystal structure was confirmed by single-crystal X-ray crystallographic analysis at 293 K and R = 0.0434 based on 910 independent. reflections. The crystal belongs to the monoclinic system, space group of P2(1) with cell dimensions a = 6.050(1) angstrom, b = 7.284(1) angstrom, c = 10.289(2) angstrom, beta = 104.69(3)degrees, D-c = 1.341 Mg cm(-3) and V= 438.9(1) angstrom(3) for Z = 2. Furthermore, the molecule has a typical C-4(1) chair conformation. Hydrogen bonds between sugar molecules are responsible for stabilizing the crystal lattice. (C) 2005 Elsevier Ltd. All rights reserved.
• 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.