methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside | 960008-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl 2-deoxy-3,4,6-tri-O-benzyl-2-(N-acetyl-N-tert-butyloxycarbonylamino)-α-D-glucopyranoside；methyl 3,4,6-tri-O-benzyl-2-[N-(tert-butoxycarbonyl)acetamido]-2-deoxy-α-D-glucopyranoside
• CAS: 960008-71-3
• 化学式: C₃₅H₄₃NO₈
• 分子量: 605.728
• InChiKey: OXTSXOSCOGRTLY-UPYFENACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 hydrazine hexahydrate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  单糖衍生物的合成与表征及糖基脯氨酰胺在不对称合成中的应用

  摘要：

  首次合成、分离和使用N-乙酰氨基葡萄糖衍生物甲基2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷(9b)的β-异头体用于合成糖基伯胺4b。糖基伯胺 5a、一对单糖衍生物 6a 和 6b 以及所有这些化合物的前体也被合成、分离并通过标准光谱方法进行了充分研究，包括 1H-1H COZY 和 HSQC 等 2D NMR 光谱实验. 然后将糖基伯胺 4a、5a、6a 和 6b 以高产率转化为相应的脯氨酰胺有机催化剂（即 1a、2a、3a 和 3b）。这些糖基脯氨酰胺有机催化剂的催化活性在各种溶剂和不同温度下的不对称羟醛反应中得到证明。

  DOI：

  10.1002/ejoc.201200522
• 作为产物：
  描述：

  甲基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient Syntheses of Methyl 2-Amino-2-Deoxy-3,4,6-Tri-O-Benzyl-α-D-Glucopyranoside and its 2-tert-Butoxycarbonylamino- and 2-Methylamino Derivatives fromN-Acetyl-D-Glucosamine

  摘要：

  The synthesis of the title compounds started with N-acetylglucosamine which was converted into the corresponding methyl glycoside and O-protected with benzyl groups. Subsequent N-protection as its N-BOC-N-acetyl derivative and sequential removal of the N-acetyl group and of the BOC group led in good yield to the target compounds in multigram amounts.

  DOI：

  10.1080/07328309908544030

文献信息

• Glucosamine-Based Primary Amines as Organocatalysts for the Asymmetric Aldol Reaction
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1021/jo1023156

  日期：2011.5.6

  Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.
• Synthesis of Tc-99m labeled glucosamino-Asp-cyclic(Arg-Gly-Asp-d-Phe-Lys) as a potential angiogenesis imaging agent
  作者：Byung Chul Lee、Hyun Ju Sung、Ji Sun Kim、Kyung-Ho Jung、Yearn Seong Choe、Kyung-Han Lee、Dae Yoon Chi

  DOI：10.1016/j.bmc.2007.08.054

  日期：2007.12

  Angiogenesis imaging agents for single photon emission computed tomography ( SPECT) play a role in diagnosing tumor-induced angiogenesis as well as tumor metastasis. We synthesized and evaluated radiolabeled RGD glycopeptides by incorporation of the [Tc-99m(CO)(3)(H2O)(3)](+) center dot Tc-99m labeled glucosamino-D-c(RGDfK) ([Tc-99m]2) was prepared in 90-93% radiochemical yields (decay corrected). In vitro cell binding assays demonstrated selective binding [Tc-99m]2 to human umbilical vein endothelial ( HUVE) cells, with inhibition of binding to 37.3% of control levels by 10 mu M of cold authentic compounds. In addition, [Tc-99m]2 was shown to have high binding affinity to purified alpha(v)beta(3) integrin (IC50 = 1.5 nM). These results suggest that these radiolabeled RGD glycopeptides may have value for non-invasive assessment of angiogenesis. (c) 2007 Elsevier Ltd. All rights reserved.