1-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene | 262286-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
• 英文别名: (2'-acetylamino-3',4',5'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene；3-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene；3-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)propene；N-[(2R,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-yl]acetamide
• CAS: 262286-48-6
• 化学式: C₃₂H₃₇NO₅
• 分子量: 515.649
• InChiKey: XGEGEVYOVYQAEX-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 sodium chlorite 、 2-甲基-2-丁烯 、 (Ph₂Me)2IrCOD*PF₆ 、 camphor-10-sulfonic acid 、 potassium carbonate 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 2.0h， 生成 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9
• 作为产物：
  描述：

  3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
  参考文献：
  名称：

  简洁的合成C-糖基磷酸酯和N-乙酰基-α-d-葡糖胺1-磷酸的膦酸酯类似物

  摘要：

  描述了一种容易制备的N-乙酰基-α-d-葡糖胺1-磷酸的C-糖基磷酸酯和膦酸酯类似物。容易获得的3-（2'-乙酰氨基-3'，4'，6'-三-O-乙酰基-2'-脱氧-α-d-吡喃吡喃糖基）-1-丙烯3已被用作常见的中间体。

  DOI：

  10.1016/s0040-4039(99)02277-7

文献信息

• Synthesis of 2-(<i>N</i>-Acetylamino)-2-deoxy-<i>C</i>-glucopyranosyl Nucleosides as Potential Inhibitors of Chitin Synthases
  作者：Jérôme Grugier、Juan Xie、Isabelle Duarte、Jean-Marc Valéry

  DOI：10.1021/jo991206p

  日期：2000.2.1

  derivatives (6a or 6b) afforded, respectively, the ester 12 and amide 14. The dihydroxylation of the conjugated double bond in ester 12 or amide 14 was better achieved with osmium tetraoxide/barium chlorate, leading to the expected diols 13 and 15 as a mixture of two diastereoisomers. The desired compounds 1-4 were obtained after catalytic hydrogenation of compounds 12-15.

  含有N-乙酰基氨基葡萄糖氨基和尿苷单元的C-吡喃葡萄糖基核苷（1-4）已被合成为UDP-GlcNAc的不可水解底物类似物，目的是抑制几丁质合酶。关键中间体4-（2'-（N-乙酰氨基）-3'，4'，6'-三-O-苄基-2'-脱氧-α-D-吡喃葡萄糖基）丁-2-烯酸（5 ）是由全苄基化（N-乙酰氨基）-α-C-烯丙基葡糖苷（7）通过连续的氧化裂解，Wittig烯化和酯脱保护制备的。酸5与尿苷衍生物（6a或6b）的羟基或胺官能团偶合，分别得到酯12和酰胺14。用能更好地实现酯12或酰胺14中共轭双键的二羟基化。四氧化物/氯酸钡，得到两种非对映异构体混合物的预期二醇13和15。化合物12-15催化氢化后，得到所需的化合物1-4。
• Regioselective debenzylation of C-glycosyl compounds by boron trichloride
  作者：Juan Xie、Mickaël Ménand、Jean-Marc Valéry

  DOI：10.1016/j.carres.2004.12.001

  日期：2005.2

  Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl(3) follows the order: C-4>or=C-2>C-6>C-3 for C-glucopyranosyl derivatives and C-3>or=C-4>C-6>C-2 for C-galactopyranosyl derivatives. Preparatively useful selective debenzylation at secondary positions was possible

  已经发现三氯化硼可促进过苄基化的C-糖基衍生物的1，2-或1，3-顺式的仲苄基醚的选择性脱保护。对BCl（3）的反应性依次为：C-4>或= C-2> C-6> C-3（对于C-吡喃葡萄糖基衍生物）和C-3>或= C-4> C-6> C- 2为C-吡喃半乳糖基衍生物。在仔细控制反应条件后，可能在次要位置上进行有用的选择性脱苄基反应。
• Synthesis of Sugar Azido or Amino Esters and Their Use as Building Blocks for the Preparation of Saccharide Nucleosides
  作者：Juan Xie

  DOI：10.1002/1099-0690(200210)2002:20<3411::aid-ejoc3411>3.0.co;2-q

  日期：2002.10

  selective removal of the primary benzyl group or selective acetolysis of the primary benzyl group of β-C-glycoside as key steps. Such structures have been successfully used as scaffolds for the synthesis of novel saccharide nucleosides. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  已经通过 TMSOTf/Ac2O 介导的 α-C-糖基化制备了几种带有 α- 或 β-CD-吡喃葡萄糖基主链的糖叠氮基或氨基酯，同时选择性去除初级苄基或选择性乙酰化初级苄基β-C-糖苷作为关键步骤。此类结构已成功用作合成新型糖核苷的支架。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• INVESTIGATION OF THE SHARPLESS ASYMMETRIC AMINOHYDROXYLATION WITH <i>C</i>-ALLYL GLYCOSIDES
  作者：Juan Xie、Jean-Marc Valéry

  DOI：10.1081/car-100106927

  日期：2001.7.31

  We have studied the Sharpless asymmetric aminohydroxylation on C-allyl glycosides in order to prepare C-glycosyl aminoacids or C-glycopeptides. The perbenzylated amino α-C-allyl glucoside 1 and β-C-allyl glucoside 2 were shown to be moderate substrates for this reaction. New C-glycosyl α-amino ketones were isolated after oxidation of the crude β-amino alcohols.

  为了制备C-糖基氨基酸或C-糖肽，我们研究了C-烯丙基糖苷的Sharpless不对称氨基羟基化反应。过苄基化的氨基α-C-烯丙基葡糖苷1和β-C-烯丙基葡糖苷2显示为该反应的中等底物。粗制β-氨基醇氧化后，分离出新的C-糖基α-氨基酮。
• Synthesis of new sugar amino acid derivatives of d-glucosamine
  作者：Juan Xie

  DOI：10.1016/s0008-6215(02)00487-1

  日期：2003.2

  The synthesis of several new sugar amino acid derivatives of 2-acetamido-2-deoxy-D-glucose, bearing a C-glycosyl functionality as building blocks for the design and synthesis of natural glycoconjugates mimetics, is described. These compounds were prepared from the readily accessible per-benzylated amino C-allyl glucopyranosyl compounds, with TMSOTf/Ac(2)O-mediated selective acetolysis of the 6-O-benzyl

  描述了几种新的2-乙酰氨基-2-脱氧-D-葡萄糖的糖氨基酸衍生物的合成，其带有C-糖基官能团，作为天然糖缀合物模拟物的设计和合成的基础。这些化合物是从容易获得的全苄基氨基C-烯丙基吡喃葡萄糖基化合物中制备的，其中TMSOTf / Ac（2）O介导的6-O-苄基的选择性乙酰水解是关键步骤。