methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside | 81872-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 81872-62-0
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: FYUXMZUFURHCOX-BXLDVZOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 methyl 3-O-<(R)-1-carboxyethyl>-α-D-galactopyranoside Na salt
  参考文献：
  名称：

  Synthesis and NMR studies of methyl 3-O-[(R)- and (S)-1-carboxyethyl]-α-d-gluco-, galacto- and manno- pyranosides

  摘要：

  The title compounds were prepared by condensation of a suitably protected monosaccharide and (R)- or (S)-2-chloropropionic acid followed by removal of the protecting groups. Characterisation by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed both chemical shift and enhancement differences between the diastereomers which could be used in determination of the absolute configuration of the l-carboxyethyl group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00272-9
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-α-D-galactopyranoside 在 sodium methylate 、 四丁基硫酸氢铵 作用下， 以 甲醇 为溶剂， 生成 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and NMR studies of methyl 3-O-[(R)- and (S)-1-carboxyethyl]-α-d-gluco-, galacto- and manno- pyranosides

  摘要：

  The title compounds were prepared by condensation of a suitably protected monosaccharide and (R)- or (S)-2-chloropropionic acid followed by removal of the protecting groups. Characterisation by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed both chemical shift and enhancement differences between the diastereomers which could be used in determination of the absolute configuration of the l-carboxyethyl group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00272-9

文献信息

• A Chiral Copper Catalyzed Site‐Selective O‐Alkylation of Carbohydrates
  作者：Bo Ren、Jiaxi Wang、Mengyao Zhang、Yue Chen、Wei Zhao

  DOI：10.1002/adsc.202101121

  日期：2022.2

  Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper catalyzed universal highly site-selective alkylation of trans-diols method is realized. This reaction is performed under mild conditions and has broad

  糖羟基的高度区域选择性烷基化一直是碳水化合物化学中的一个重要挑战，尤其是反式二醇的选择性烷基化，目前还没有直接有效的催化方法。实现了一种手性铜催化的反式二醇通用高位点选择性烷基化方法。该反应条件温和，底物范围广。反应的选择性可以通过调节铜试剂和手性配体来控制。该方法也应用于药物和天然产物的位点选择性修饰。
• Solvent-free benzylation of polyols by phase-transfer catalysis or supported reagent methods
  作者：Didier Dubreuil、Jeannine Cleophax、André Loupy

  DOI：10.1016/0008-6215(94)90012-4

  日期：1994.1

  Abstract Solvent-free techniques were successfully and efficiently applied under mild conditions to the perbenzylation of methyl α- d -glucopyranoside and methyl 6-bromo(and 6-chloro)-6-deoxy-α- d -glucopyranoside, and to the selective monobenzylation of diethyl (R,R)-tartrate. Selective 2-O- or 3-O-benzylation of methyl 4,6-O-benzylidene-α- d -galactopyranoside, requiring CH2Cl2 as solvent, was observed

  摘要在温和条件下成功，有效地将无溶剂技术应用于甲基α-d-吡喃葡萄糖苷和甲基6-溴（和6-氯）-6-脱氧-α-d-吡喃葡萄糖苷的过苄基化反应以及选择性的单苄基化反应（R，R）-酒石酸二乙酯 根据铵催化剂的性质，观察到需要CH 2 Cl 2作为溶剂的甲基4，6-O-亚苄基-α-d-吡喃半乳糖苷的选择性2-O-或3-O-苄基化。
• Regioselective alkylation of carbohydrates in metal complexes
  作者：Ronald Eby、Conrad Schuerch

  DOI：10.1016/s0008-6215(00)81068-x

  日期：——
• Alkylation of methyl 4,6-O-benzylidene-α-D-galactopyranoside
  作者：V. I. Grishkovets、V. Ya. Chirva

  DOI：10.1007/bf00581589

  日期：1982.1