(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 | 887326-77-4

• 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-[(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
• CAS: 887326-77-4
• 化学式: C₄₂H₆₃NO₁₁Si₂
• 分子量: 814.133
• InChiKey: HGLFDZINIHUXFG-NWUDYKKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  140.24
• 氢给体数：
  2.0
• 氢受体数：
  11.0

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-[(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 在 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 生成 [(2S,3R,4S,5R,6S)-6-[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[4-[(2R)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenoxy]oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] 3-methylbutanoate
  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：

  (2S,6S)-carbonic acid tert-butyl ester 6-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester 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-[(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