(S)-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidin-2-one | 236755-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidin-2-one
• CAS: 236755-07-0
• 化学式: C₃₉H₄₁NO₇
• 分子量: 635.757
• InChiKey: PKWNMFDWROKZPH-OHKUXPBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.48
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidin-2-one 在 4-二甲氨基吡啶 、 sodium acetate 、 苯硫酚 、 三乙胺 、 对甲苯磺酰肼 、 三氟乙酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 (S)-2-Amino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butan-1-ol
  参考文献：
  名称：

  Synthesis of carbon-linked glycopeptides as stable glycopeptide models

  摘要：

  A C-glycosyl analog of beta-Gal-O-Ser has been synthesized and incorporated by automated solid-phase peptide synthesis into a hydrolytically stable, alpha-helical C-glycopeptide.

  DOI：

  10.1021/jo00049a005
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal 、 ((R)-2-Oxo-oxazolidin-4-ylmethyl)-triphenyl-phosphonium 在 正丁基锂 作用下， 生成 (S)-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of carbon-linked glycopeptides as stable glycopeptide models

  摘要：

  A C-glycosyl analog of beta-Gal-O-Ser has been synthesized and incorporated by automated solid-phase peptide synthesis into a hydrolytically stable, alpha-helical C-glycopeptide.

  DOI：

  10.1021/jo00049a005

文献信息

• Synthesis of β-<scp>d</scp>-Galactosyl Ceramide Methylene Isostere
  作者：Alessandro Dondoni、Daniela Perrone、Elisa Turturici

  DOI：10.1021/jo990398l

  日期：1999.7.1

  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.