(((2R,3R,4R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl-6-d)bis(oxy))bis(tert-butyldimethylsilane) | 104016-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (((2R,3R,4R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl-6-d)bis(oxy))bis(tert-butyldimethylsilane)
• CAS: 104016-88-8
• 化学式: C₂₄H₅₄O₄Si₃
• 分子量: 491.939
• InChiKey: CTIOZUCRMBTLDJ-LZQWSINLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  phenylsulfonyl 3,4,6-tri-O-butyldimethylsilyl-2-deoxy-α,β-D-arabino-hexopyranoside 生成 (((2R,3R,4R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl-6-d)bis(oxy))bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  D-glycopyranosyl phenylsulfones: Their use in a stereocontrolledsynthesis of cis-2,6-disubstituted tetrahydropyrans (β-d-c-clycosides)

  摘要：

  DOI：

  10.1016/s0040-4039(00)95049-4

文献信息

• Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides
  作者：Jean-Marie Beau、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)95048-2

  日期：1985.1

  2-Deoxy-D-glucopyranosyl phenylsulfones 3a–c have been synthesized in 75–83% yield from commercial tri-O-acetyl-D-glucal 1. Their reductive desulfonylation by lithium naphthalenide and reaction of the intermediate glycosyl-lithium 5 with aldehydes leads to α-D-C-glucopyranosides with high stereoselectivity.

  2-脱氧-D-吡喃葡萄糖基苯基砜3a-c已从商品三-O-乙酰基-D-葡萄糖1合成，产率为75-83％。它们通过萘二甲酸锂的还原性脱磺酰基作用以及中间体糖基锂5与醛的反应导致具有高立体选择性的α-DC-吡喃葡萄糖苷。