N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide | 677334-81-5

• 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: N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide
• 英文别名: N-((3R,4R,5R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide；N-[(3S,4R,5R,6R)-6-hydroxy-4,5,7-tris(phenylmethoxy)hept-1-en-3-yl]acetamide
• CAS: 677334-81-5
• 化学式: C₃₀H₃₅NO₅
• 分子量: 489.612
• InChiKey: NMXVSQMQVBRBMT-MIPYOGIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide 在 palladium on activated charcoal 盐酸 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 氢气 、 二正丁基氧化锡 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 生成 N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide
  参考文献：
  名称：

  Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A

  摘要：

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.135
• 作为产物：
  描述：

  N-(4-Methoxy-benzyl)-N-((1S,2R,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-1-vinyl-pentyl)-acetamide 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 为溶剂， 以49%的产率得到N-((3S,4R,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-1-en-3-yl)acetamide
  参考文献：
  名称：

  Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A

  摘要：

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.135

文献信息

• Iminosugar C-Glycoside Analogues of α-<scp>d</scp>-GlcNAc-1-Phosphate: Synthesis and Bacterial Transglycosylase Inhibition
  作者：Che-Hsiung Hsu、Mathias Schelwies、Sebastian Enck、Lin-Ya Huang、Shih-Hsien Huang、Yi-Fan Chang、Ting-Jen Rachel Cheng、Wei-Chieh Cheng、Chi-Huey Wong

  DOI：10.1021/jo501340s

  日期：2014.9.19

  We herein describe the first synthesis of iminosugar C-glycosides of α-D-GlcNAc-1-phosphate in 10 steps starting from unprotected D-GlcNAc. A diastereoselective intramolecular iodoamination-cyclization as the key step was employed to construct the central piperidine ring of the iminosugar and the C-glycosidic structure of α-D-GlcNAc. Finally, the iminosugar phosphonate and its elongated phosphate analogue were accessed. These phosphorus-containing iminosugars were coupled efficiently with lipophilic monophosphates to give lipid-linked pyrophosphate derivatives, which are lipid II mimetics endowed with potent inhibitory properties toward bacterial transglycosylases (TGase).
• Stereoselective Synthesis of α-<i>C</i>-Glucosyl Serine and Alanine via a Cross-Metathesis/Cyclization Strategy
  作者：Ernest G. Nolen、Adam J. Kurish、Jennifer M. Potter、Lawrence A. Donahue、Michael D. Orlando

  DOI：10.1021/ol051341q

  日期：2005.7.1

  C-Glycosyl amino acids represent stable mimics of monomeric units within natural O-linked glycoproteins. Olefin cross-metathesis has been used to provide alkene precursors for a mercury(II)-mediated cyclization, yielding alpha-C-glucosyl serine and alanine.
• Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A
  作者：Hidemi Yoda、Yuji Suzuki、Kunihiko Takabe

  DOI：10.1016/j.tetlet.2003.12.135

  日期：2004.2

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.