benzyl 3,6-di-O-benzyl-β-D-glucopyranoside | 383406-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,6-di-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-3,5-diol
• CAS: 383406-90-4
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: DFQOHFUZUTWKPI-KUDLYRENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3,6-di-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 156.0h， 生成 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)]-1,3,6-tri-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis of peracetylated chacotriose

  摘要：

  Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety alpha -L-rhamnopyranosyl-(1 -->2)-[alpha -L-rhamnopyranosyl-(1 -->4)]-D-glucopyranose (chacotriose) whose peracetate is here synthesized and characterized by complete H-1 and C-13 NMR assignment. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00193-8
• 作为产物：
  描述：

  3,6-di-O-benzyl-D-glucopyranose 在 吡啶 、 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 benzyl 3,6-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of peracetylated chacotriose

  摘要：

  Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety alpha -L-rhamnopyranosyl-(1 -->2)-[alpha -L-rhamnopyranosyl-(1 -->4)]-D-glucopyranose (chacotriose) whose peracetate is here synthesized and characterized by complete H-1 and C-13 NMR assignment. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00193-8

文献信息

• Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides
  作者：Yann Bourdreux、Aurélie Lemétais、Dominique Urban、Jean-Marie Beau

  DOI：10.1039/c0cc04398b

  日期：——

  Tandem catalysis by using iron(III) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.

  通过使用六水合氯化铁（III）进行串联催化可导致碳水化合物构件显示出正交的保护基团模式，如海藻糖和麦芽糖二糖的区域选择性保护所示。
• Synthesis of peracetylated chacotriose
  作者：Marielba Morillo、Vincent Lequart、Eric Grand、Gérard Goethals、Alfredo Usubillaga、Pierre Villa、Patrick Martin

  DOI：10.1016/s0008-6215(01)00193-8

  日期：2001.9

  Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety alpha -L-rhamnopyranosyl-(1 -->2)-[alpha -L-rhamnopyranosyl-(1 -->4)]-D-glucopyranose (chacotriose) whose peracetate is here synthesized and characterized by complete H-1 and C-13 NMR assignment. (C) 2001 Elsevier Science Ltd. All rights reserved.