phenyl 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-1-thio-β-D-ribohexapyranoside | 1512846-84-2

• 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: phenyl 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-1-thio-β-D-ribohexapyranoside
• 英文别名: TBDMS(-3)[Mob(-4)]Dig(b)-SPh；tert-butyl-[(2R,3R,4S,6S)-3-[(4-methoxyphenyl)methoxy]-2-methyl-6-phenylsulfanyloxan-4-yl]oxy-dimethylsilane
• CAS: 1512846-84-2
• 化学式: C₂₆H₃₈O₄SSi
• 分子量: 474.737
• InChiKey: ZYGXJBXEVAWQJW-LJYZBVLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-1-thio-β-D-ribohexapyranoside 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 、 mineral oil 为溶剂， 反应 24.42h， 生成 phenyl 2,6-dideoxy-4-O-p-methoxybenzyl-α-D-ribo-hexapyranosyl-(1→4)-3-O-p-methoxybenzyl-2,6-dideoxy-1-thio-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  通过螯合控制的端基O-烷基化立体选择性合成α-二氨基葡萄糖苷和α- Boivinosides

  摘要：

  已经开发了螯合控制的异头O-烷基化反应，用于立体选择性地合成α-数字氧苷和带有C3-游离羟基的α-boivinosides。由于经由钠离子的螯合，异头醇盐被锁定在轴向构型中，这导致选择性产生α-糖苷。

  DOI：

  10.1080/07328303.2014.931965
• 作为产物：
  描述：

  1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol 在 咪唑 、 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.0h， 生成 phenyl 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-1-thio-β-D-ribohexapyranoside
  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.
• Stereoselective Synthesis of α-Digitoxosides and α-Boivinosides via Chelation-Controlled Anomeric<i>O</i>-Alkylation
  作者：Danyang Zhu、Surya Adhikari、Kedar N. Baryal、Belal N. Abdullah、Jianglong Zhu

  DOI：10.1080/07328303.2014.931965

  日期：2014.10.13

  A chelation-controlled anomeric O-alkylation has been developed for the stereoselective synthesis of α-digitoxosides and α-boivinosides bearing a C3-free hydroxyl group. Due to chelation via sodium ion, the anomeric alkoxides are locked in the axial configuration, which leads to the selective production of α-glycosides.

  已经开发了螯合控制的异头O-烷基化反应，用于立体选择性地合成α-数字氧苷和带有C3-游离羟基的α-boivinosides。由于经由钠离子的螯合，异头醇盐被锁定在轴向构型中，这导致选择性产生α-糖苷。