(2S,3R,4S,5S,6R)-4-(benzyloxy)-2,3,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran | 39708-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-4-(benzyloxy)-2,3,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran
• 英文别名: methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside)；Methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranosid)
• CAS: 39708-09-3；39708-10-6；69412-16-4
• 化学式: C₁₇H₂₆O₆
• 分子量: 326.39
• InChiKey: SGVYYYJIXWXTQA-VDWCLKJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-4-(benzyloxy)-2,3,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran 在 palladium on activated charcoal 氢气 作用下， 生成 methyl 2,4,6-tri-O-methyl-α,β-D-glucopyranoside
  参考文献：
  名称：

  Studies of model compounds for the analysis of ester-containing polysaccharides by the reductive-cleavage method

  摘要：

  The four O-propionyl regioisomers of methyl tri-O-methyl-alpha-D-glucopyranoside and the 2- and 3-O-propionyl regioisomers of methyl tri-O-methyl-beta-D-glucopyranoside were subjected to reductive cleavage in the presence of Et3SiH and Me3SiOSO2CF3, BF3.Et2O, or Me3SiOSO2Me-BF3.Et2O. The O-propionyl group was stable when either Me3SiOSO2CF3 or BF3.Et2O Was the catalyst, but was slowly reduced to the (1-propyl) ether when Me3SiOSO2Me-BF3.Et2O was the catalyst. Reductive cleavages catalyzed by Me3SiOSO2CF3 were complete in 6 h, those catalyzed by BF3.Et2O required at least 24 h, and those catalyzed by Me3SiOSO2Me-BF3.Et2O required 30 min or less. In the alpha-series, the rate of reductive cleavage decreased in the order 6-O-propionyl > 4-O-propionyl > 3-O-propionyl much greater than 2-O-propionyl. The reductive cleavage of beta-anomers was faster than that of the corresponding alpha-anomers. This effect was particularly striking for the alpha and beta-anomers of the 2-O-propionyl regioisomer, as would be expected on the basis of a participation reaction.

  DOI：

  10.1016/0008-6215(92)84021-j
• 作为产物：
  描述：

  1,2,4,6-四-o-乙酰基-3-o-苄基-beta-d-吡喃葡萄糖 、 硫酸二甲酯 在 氢氧化钾 作用下， 生成 (2S,3R,4S,5S,6R)-4-(benzyloxy)-2,3,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Freudenberg; Plankenhorn, Justus Liebigs Annalen der Chemie, 1938, vol. 536, p. 257,260

  摘要：

  DOI：

文献信息

• Kuhn et al., Chemische Berichte, 1957, vol. 90, p. 203,216
  作者：Kuhn et al.

  DOI：——

  日期：——
• Epimerization in the Synthesis of 2,4,6-Tri-O-methyl-D-mannose¹
  作者：N. Prentice、L. S. Cuendet、F. Smith

  DOI：10.1021/ja01598a065

  日期：1956.9