phenyl 3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribo-hexopyranoside | 1512847-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribo-hexopyranoside
• 英文别名: Bn(-3)Dig(b1-4)[Bn(-3)]6-deoxy-All2Me(a)-SPh；(2R,3R,4S,6S)-6-[(2R,3R,4R,5R,6R)-5-methoxy-2-methyl-4-phenylmethoxy-6-phenylsulfanyloxan-3-yl]oxy-2-methyl-4-phenylmethoxyoxan-3-ol
• CAS: 1512847-00-5
• 化学式: C₃₃H₄₀O₇S
• 分子量: 580.742
• InChiKey: WCYAGSJNEIPBFP-AEEYDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribo-hexopyranoside 在 咪唑 、 LiDBB 、 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 100.25h， 生成 3,4-Di-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-1,5-anhydro-3-O-tert-butyldimethylsilyl-2,6-dideoxy-D-ribo-hex-1-enitol
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-benzylallopyranose 在 lithium aluminium tetrahydride 、 [ReOCl3(OPPh3)(SMe2)] 、 三氟化硼乙醚 、 二苯基酸 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 124.75h， 生成 phenyl 3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419

文献信息

• Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin
  作者：Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/jo4021419

  日期：2013.12.20

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.