methyl (2R)-3-[4-[[(2S,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate | 887326-68-3

• 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: methyl (2R)-3-[4-[[(2S,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 887326-68-3
• 化学式: C₄₂H₆₁NO₁₁Si₂
• 分子量: 812.117
• InChiKey: STPZHFFGUIARHF-UQFJHEGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2R)-3-[4-[[(2S,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl]oxy]-3,6-dihydro-2H-pyran-6-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate 在 sodium tetrahydroborate 作用下， 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：

  (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 methyl (2R)-3-[4-[[(2S,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[[(2R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-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.