2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole | 236388-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole
• CAS: 236388-80-0
• 化学式: C₄₅H₄₅NO₆
• 分子量: 695.855
• InChiKey: VLUZBZIBLUAKCT-HJKGUNCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole 在 盐酸 、 4-二甲氨基吡啶 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 吡啶 为溶剂， 反应 34.0h， 生成 Acetic acid (R)-2-benzoylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester
  参考文献：
  名称：

  Synthesis of β-d-Galactosyl Ceramide Methylene Isostere

  摘要：

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.

  DOI：

  10.1021/jo990398l
• 作为产物：
  描述：

  (R)-4-(iodomethyl)-2-phenyl-2-oxazoline 在 正丁基锂 、 4 Angstroem MS 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole
  参考文献：
  名称：

  Synthesis of β-d-Galactosyl Ceramide Methylene Isostere

  摘要：

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.

  DOI：

  10.1021/jo990398l