methyl (2R)-3-[4-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate | 887326-66-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R)-3-[4-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 887326-66-1
• 化学式: C₄₂H₆₃NO₁₁Si₂
• 分子量: 814.133
• InChiKey: HGLFDZINIHUXFG-WDDJQPBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2R)-3-[4-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate 在 bis(η3-allyl-μ-chloropalladium(II)) 吡啶 、 4-二甲氨基吡啶 、 三丁基膦 、 叠氮基三甲基硅烷 、 N,N'-二环己基碳二亚胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成 methyl (2R)-3-[4-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2S,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(3-methylbutanoylamino)-3,6-dihydro-2H-pyran-6-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  甘露肽霉素E的糖基化酪氨酸部分氮杂类似物的合成

  摘要：

  通过迭代的钯糖基化序列合成了甘露肽霉素-E的两个C 4'酰胺二糖类似物。从受保护的d-酪氨酸经过十个步骤完成了C 4'酰化的1，4-α，α-甘露聚糖，甘露糖酰胺基二糖的立体选择性合成。该路径依赖于区域和非对映选择性钯催化的叠氮化物取代反应。合成的能力由受保护的酪氨酸的良好总收率（21％）证明。

  DOI：

  10.1021/jo070326r
• 作为产物：
  描述：

  methyl (2R)-3-[4-[[(2R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (2R)-3-[4-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Synthetic Studies toward Mannopeptimycin-E:  Synthesis of the O-Linked Tyrosine 1,4-α,α-manno,manno-Pyranosyl Pyranoside

  摘要：

  The enantioselective synthesis of the C-4' acylated 1,4-alpha,alpha-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from D-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues.

  DOI：

  10.1021/ol060254a

文献信息

• Synthetic Studies toward Mannopeptimycin-E:  Synthesis of the <i>O</i>-Linked Tyrosine 1,4-α,α-<i>manno,manno</i>-Pyranosyl Pyranoside
  作者：Ravula Satheesh Babu、Sanjeeva R. Guppi、George A. O'Doherty

  DOI：10.1021/ol060254a

  日期：2006.4.1

  The enantioselective synthesis of the C-4' acylated 1,4-alpha,alpha-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from D-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues.
• Synthesis of Aza-Analogues of the Glycosylated Tyrosine Portion of Mannopeptimycin-E
  作者：Sanjeeva R. Guppi、George A. O'Doherty

  DOI：10.1021/jo070326r

  日期：2007.6.1

  Two C4‘ amido disaccharide analogues of mannopeptimycin-E were synthesized via an iterative palladium glycosylation sequence. The stereoselective synthesis of the C4‘ acylated 1,4-α,α-manno,manno-amido disaccharide has been achieved in ten steps from a protected d-tyrosine. The path relies upon a regio- and diastereoselective palladium-catalyzed azide substitution reaction. The competence of the synthesis

  通过迭代的钯糖基化序列合成了甘露肽霉素-E的两个C 4'酰胺二糖类似物。从受保护的d-酪氨酸经过十个步骤完成了C 4'酰化的1，4-α，α-甘露聚糖，甘露糖酰胺基二糖的立体选择性合成。该路径依赖于区域和非对映选择性钯催化的叠氮化物取代反应。合成的能力由受保护的酪氨酸的良好总收率（21％）证明。