(S)-4-[2-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 536739-83-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-[2-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 536739-83-0
• 化学式: C₄₀H₅₁NO₈
• 分子量: 673.847
• InChiKey: FTZJNNRCLOACHS-IQDMKPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  49.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[2-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 lead(II) chloride 四甲基乙二胺 、 硼烷 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 tert-butyl (4S)-4-[2-[(2S,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Some Biologically Relevant β-C-Glycoconjugates

  摘要：

  [GRAPHICS]An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.

  DOI：

  10.1021/ol034363q
• 作为产物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 、 (4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(S)-4-[2-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  RCM-Based Synthesis of a Variety of β-C-Glycosides and Their in Vitro Anti-Solid Tumor Activity

  摘要：

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo040254t