(R)-2-Benzyloxycarbonylamino-3-{4-[(2S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester | 887326-76-3

• 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: (R)-2-Benzyloxycarbonylamino-3-{4-[(2S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester
• CAS: 887326-76-3
• 化学式: C₃₀H₄₁NO₈Si
• 分子量: 571.743
• InChiKey: HMDHQKJUXRVYMK-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Benzyloxycarbonylamino-3-{4-[(2S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-2-Benzyloxycarbonylamino-3-(4-{(2S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-[(2R,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yloxy]-5,6-dihydro-2H-pyran-2-yloxy}-phenyl)-propionic acid methyl ester
  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
• 作为产物：
  描述：

  Z-D-酪氨酸甲基酯 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 (R)-2-Benzyloxycarbonylamino-3-{4-[(2S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester
  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