(S)-2-Benzyloxycarbonylamino-3-{4-[(2S,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester | 623157-79-9

• 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: (S)-2-Benzyloxycarbonylamino-3-{4-[(2S,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester
• 英文别名: methyl (2S)-3-[4-[[(2S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 623157-79-9
• 化学式: C₃₀H₃₉NO₈Si
• 分子量: 569.727
• InChiKey: FPSOQIIWWBLSPV-DOEKTCAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-3-{4-[(2S,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yloxy]-phenyl}-propionic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(S)-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
• 作为产物：
  描述：

  Z-L-酪氨酸甲酯 、 (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 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(S)-2-Benzyloxycarbonylamino-3-{4-[(2S,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-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

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.