phenyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside | 1512847-02-7

• 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-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside
• 英文别名: Bn(-3)[TBDMS(-4)]Dig(b1-4)[Bn(-3)]Dig(b1-4)[Bn(-3)]6-deoxy-All2Me(a)-SPh；tert-butyl-[(2R,3R,4S,6S)-6-[(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-yl]oxy-2-methyl-4-phenylmethoxyoxan-3-yl]oxy-dimethylsilane
• CAS: 1512847-02-7
• 化学式: C₅₂H₇₀O₁₀SSi
• 分子量: 915.273
• InChiKey: OPNBZHBUSUMDNW-DRUSRQGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.73
• 重原子数：
  64.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到Bn(-3)Dig(b1-4)[Bn(-3)]Dig(b1-4)[Bn(-3)]6-deoxy-All2Me(a)-SPh
  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 184.75h， 生成 phenyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside 、 Tert-butyl-[(2R,3R,4S,6R)-6-[(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-yl]oxy-2-methyl-4-phenylmethoxyoxan-3-yl]oxy-dimethylsilane
  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.