isopropyl-6-O-trimethylacetyl-3-[hydroxy-(4-cyanophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose | 945030-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isopropyl-6-O-trimethylacetyl-3-[hydroxy-(4-cyanophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose
• 英文别名: [(2S,6R)-4-[(R)-(4-cyanophenyl)-hydroxymethyl]-5-oxo-2-propan-2-yloxy-2H-pyran-6-yl]methyl 2,2-dimethylpropanoate
• CAS: 945030-48-8
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: UDIMSJUXGWDCNG-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  isopropyl-6-O-trimethylacetyl-3-[hydroxy-(4-cyanophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  Regioselective synthesis of densely functionalized, enantiopure, sugar–pyrazole hybrids as potential scaffolds for drug discovery

  摘要：

  报道了一种利用MBH化学的新型多功能合成策略，用于组装具有多个结构多样化位点和非平面骨架的高度官能化手性纯糖-吡唑杂化分子，这些分子可作为潜在药物骨架。通过筛选四种代表性杂化分子在体外抗肿瘤活性，发现其中三种表现出良好的抗肿瘤活性。

  DOI：

  10.1039/c3ra22287j
• 作为产物：
  描述：

  isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 吡啶 、 manganese(IV) oxide 、 sodium methylate 、 四氯化钛 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 50.0h， 生成 isopropyl-6-O-trimethylacetyl-3-[hydroxy-(4-cyanophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose
  参考文献：
  名称：

  C-3 Alkyl/Arylalkyl-2,3-dideoxy Hex-2-enopyranosides as Antitubercular Agents:  Synthesis, Biological Evaluation, and QSAR Study

  摘要：

  A series of C-3 alkyl and arylalkyl 2,3-dideoxy hex-2-enopyranoside derivatives were synthesized by Morita-Baylis-Hillman reaction using enulosides 4,5, and 6 and various aliphatic and aromatic aldehydes. The compounds were evaluated in vitro for the complete inhibition of growth of Mycobacterium tuberculosis H37Rv. They exhibited moderate to good activity in the range of 25-1.56 mu g/mL. Among these, 4d, 4h, 5c, and 4hr showed activity at minimum inhibitory concentrations, 3.12, 6.25, 1.56, and 1.56 mu g/mL, respectively. These compounds were safe against cytotoxicity in VERO cell line and mouse macrophage cell line J 744A.1. A QSAR analysis by CP-MLR with alignment-free 3D-descriptors indicated the relevance of structure space comparable to the minimum energy conformation (from conformational analysis) of 5c to the activity. The study indicates that the compounds attaining the conformational space of 5c and reflecting some symmetry, minimum eccentricity, and closely placed geometric and electronegativity centers therein are favorable for activity.

  DOI：

  10.1021/jm070110h

文献信息

• Facile Synthesis of Enantiomerically Pure 2- and 2,3-Disubstituted Furans Catalysed by Mixed Lewis Acids: An Easy Route to 3-Iodofurans and 3-(Hydroxymethyl)furans
  作者：Mohammad Saquib、Irfan Husain、Brijesh Kumar、Arun K. Shaw

  DOI：10.1002/chem.200900007

  日期：2009.6.8

  Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl4/ZnI2), of enantiomerically pure 2‐ and 2,3‐disubstituted furan derivatives, including 3‐iodofuran and 3‐ (hydroxymethyl)furan derivatives, in good to very good yields from commercially available 3,4,6‐tri‐O‐acetyl‐D‐glucal is described. Key features of this method are the use of inexpensive reagents in catalytic amounts

  对映纯呋喃合成：由混合路易斯酸（ZrCl 4 / ZnI 2）催化的对映体纯的2和2,3-二取代呋喃衍生物，包括3-碘呋喃和3-（羟甲基）呋喃衍生物描述了从商业上可获得的3,4,6- tri - O-乙酰基-D-葡萄糖的非常好的收率。该方法的主要特点是使用廉价的催化量试剂，温和的反应条件和简便的后处理程序。