(2,3,5-tri-O-benzyl-D-arabinofuranosyl)-benzylamine | 151593-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,5-tri-O-benzyl-D-arabinofuranosyl)-benzylamine
• 英文别名: N-benzyl-2,3,5-tri-O-benzyl-D-arabinofuranosylamine；2,3,5-tri-O-benzyl-N-benzyl-D-arabinosylamine；N-benzyl-2,3,5-tri-O-ben-zyl-d-arabinofuranosylamine；(3S,4R,5R)-N-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-amine
• CAS: 151593-17-8
• 化学式: C₃₃H₃₅NO₄
• 分子量: 509.645
• InChiKey: IMHITWXSYMTQBM-JOYOFOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3,5-tri-O-benzyl-D-arabinofuranosyl)-benzylamine 在 N-碘代丁二酰亚胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N-benzyl-4,5,7-tri-O-benzyl-1,3-dideoxy-1,3-imino-D-glycero-D-ido-heptitol
  参考文献：
  名称：

  Reinvestigation of the iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-d-gluco-hept-1-enitol: unexpected formation of a 1,3-imino-heptitol derivative

  摘要：

  The NIS-mediated iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2.3-trideoxy-D-gluco-hept-1-enitol gave unexpectedly a 1,3-imino-heptitol derivative, namely 2-O-acetyl-N-benzyl-4,5,7-tri-O-benzyl-1,3-dideoxy-1,3-imino-D-glycero-D-ido-heptitol. This compound is a new example of a rare class of azetidine imino alditol derivatives which have interesting properties such as glycosidase inhibitors. The physical and spectral data for this imino heptitol were essentially identical to those reported for 2,6-anhydro-4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-3-deoxy-D-glycero-D-ido-heptitol, a derivative of C-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)methanol obtained from the same precursor [Lay, L.; Nicotra, F.; Panza, L.; Verani, A. Gazz,. Chim. Ital. 1992, 122, 345-348]; these findings cast doubts on the structure reported for the latter product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00314-7
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃阿拉伯糖 、 苄胺 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以90%的产率得到(2,3,5-tri-O-benzyl-D-arabinofuranosyl)-benzylamine
  参考文献：
  名称：

  糖胺上的格氏反应合成氮杂糖

  摘要：

  吡咯烷5a-b以及哌啶10a，b和15是通过在糖基胺上进行格氏反应合成的，该糖基胺很容易从母体糖和伯胺中获得，然后用三氟甲磺酸酐环化。

  DOI：

  10.1016/0040-4020(95)00151-w

文献信息

• A new procedure for the synthesis of<scp>D</scp>-glucosamine α-C-glycosides
  作者：Marta Carcano、Francesco Nicotra、Luigi Panza、Giovanni Russo

  DOI：10.1039/c39890000297

  日期：——

  Reaction of (2,3,5-tri-O-benzyl-D-arabinofuranosyl)benzylamine with vinylmagnesium bromide and subsequent mercuriocyclisation of the obtained open-chain product, provides a stereoselective entry to α-C-glycosides of D-glucosamine.

  （2,3,5-三-O-苄基-D-阿拉伯呋喃糖基）苄胺与乙烯基溴化镁的反应以及随后获得的开链产物的巯基环化，为D-葡糖胺的α- C-糖苷提供了立体选择性入口。
• A new procedure for the synthesis of azasugars
  作者：Luigi Lay、Francesco Nicotra、Angelo Paganini、Cristina Pangrazio、Luigi Panza

  DOI：10.1016/0040-4039(93)88084-v

  日期：1993.7

  Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced

  市售的2,3,5-三-O-苄基-D-阿拉伯糖与伯胺（RNH 2）的反应得到阿拉伯呋喃糖胺2，在用格利雅试剂处理后立体选择性地得到氨基醇3。3是氮杂糖的有用前体：通过用Tf 2 O-Py处理可将其转化为吡咯烷4，而通过PCC氧化可提供可还原为相应胺6的内酰胺5。
• En Route to Novel Furanoside Mimics through Stereoselective Zinc-Mediated Propargylation of N-Benzyl Glycofuranosylamines Using Ultrasound Activation
  作者：Olivier Martin、Cyril Nicolas、Francis Engo-Ilanga、Chloé Cocaud

  DOI：10.1055/s-0034-1379551

  日期：——

  Preliminary results on a novel zinc-mediated, ultrasoundpromoted chain extension of glycofuranosylamines with a propargyl group are reported. The procedure was applied to D-arabino and D-xylo substrates to give, via Cram-chelate transition states, 1-C-1-(3-trimethylsilyl-2-propynyl)-1-benzylamino pentionols in moderate to good yields and acceptable stereoselectivities (syn/anti >= 4: 1). To apply the reaction to the synthesis of galactofuranoside mimics, the D-xylo intermediate was cyclized to afford a 1-C-1-(2-propynyl)-1,4-dideoxy-1,4-imino-L-arabinitol derivative in excellent yield. This building block was used in three examples of CuAAC click reactions with azide compounds to provide the corresponding galactofuranoside mimics.
• Behr, Jean-Bernard; Evina, Claude Mvondo; Phung, Nga, Journal of the Chemical Society. Perkin transactions I, 1997, # 11, p. 1597 - 1599
  作者：Behr, Jean-Bernard、Evina, Claude Mvondo、Phung, Nga、Guillerm, Georges

  DOI：——

  日期：——
• Oxaphosphinanes: New Therapeutic Perspectives for Glioblastoma
  作者：Ludovic Clarion、Carine Jacquard、Odile Sainte-Catherine、Séverine Loiseau、Damien Filippini、Marie-Hélène Hirlemann、Jean-Noël Volle、David Virieux、Marc Lecouvey、Jean-Luc Pirat、Norbert Bakalara

  DOI：10.1021/jm201428a

  日期：2012.3.8

  This paper reports the design and the synthesis of a new family of compounds, the phostines, belonging to the [1,2]oxaphosphinane family. Twenty-six compounds have been screened for their antiproliferative activity against a large panel of NCI cancer cell lines. Because of its easy synthesis and low EC50 value (500 nM against the C6 rat glioma cell line); compound 3.1a was selected for further biological study. Moreover, the specific biological effect of 3.1a on the glioblastoma phylogenetic cluster from the NCI is dependent on its stereochemistry. Within that cluster, 3.1a has a higher antiproliferative activity than Temozolomide and is more potent than paclitaxel for the SF295 and SNB75 cell lines. In constrast with paclitaxel and vincristine, 3.1a is devoid of astrocyte toxicity. The original activity spectrum of 3.1a on the NCI cancer cell line panel allows the development of this family for use in association with existing drugs, opening new therapeutic perspectives.