methyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-mannopyranoside | 97906-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-mannopyranoside
• 英文别名: methyl 4,6-O-benzylidene-2,3-deoxy-2,3-diamino-α-D-mannoside；Methyl-(2,3-diamino-4,6-O-benzyliden-2,3-didesoxy-α-D-mannopyranosid)；(4aR,6S,7S,8R,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diamine
• CAS: 97906-69-9
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: AIOJNMKYPYMIQY-ZWVDJKGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-mannopyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-N⁷,N⁸-bis-(2,4,6-trimethyl-benzyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diamine
  参考文献：
  名称：

  Novel chiral diimines and diamines derived from sugars in copper-catalysed asymmetric cyclopropanation

  摘要：

  New chiral diimino and diamino ligands derived from alpha -D-mannose and alpha -D-glucose are described. The ligands are obtained by introducing the appropriate nitrogen functions at C(2) and C(3) of the sugar rings. The ability of the new chelates to promote the asymmetric copper(I)-catalysed cyclopropanation of styrene has been investigated. The nature of both the sugars and the chelates is crucial in determining the enantioselectivity of the reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00438-4

文献信息

• Catalytic Diamino‐Sugar‐Assisted Enantioselective Hydrogenation
  作者：Matthias Böge、Jürgen Heck

  DOI：10.1002/ejic.201500306

  日期：2015.6

  have been studied in transition-metal-catalyzed hydrogenations in recent decades. Herein, we report the diastereoselective synthesis of trans-dichlorido(bisphosphane)ruthenium(II) complexes with four different methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-hexopyranosides and their application as catalyst precursors in asymmetric hydrogenation reactions. Depending on the hexopyranose, an enantiomeric

  近几十年来，人们在过渡金属催化的氢化反应中研究了碳水化合物配体。在此，我们报告了具有四种不同甲基 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-hexopyranosides 的反式二氯（双膦）钌（II）配合物的非对映选择性合成及其在不对称加氢反应中作为催化剂前体的应用。取决于吡喃己糖，获得了高达 78% 的对映体过量。
• Bis(phosphinoamides) based on sugars for highly enantioselective allylic substitution: inversion of stereocontrol by switching from glucose to mannose
  作者：Francesco Ruffo、Raffaella Del Litto、Antonella De Roma、Alessandra D’Errico、Santo Magnolia

  DOI：10.1016/j.tetasy.2006.07.032

  日期：2006.9

  New chiral bis(phosphinoamides) based on glucose 1G and mannose 1M have been prepared. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopenten-2-ene-1,4-diol biscarbamate in high ee's (up to 97%). Glucose and mannose moieties selectively promote formation of the opposite enantiomers, as a consequence of inverted steric motifs around the metal center. (c) 2006 Elsevier Ltd. All rights reserved.
• Mn(III) complexes of chiral ‘salen’ type ligands derived from carbohydrates in the asymmetric epoxidation of styrenes
  作者：Carmela Borriello、Raffaella Del Litto、Achille Panunzi、Francesco Ruffo

  DOI：10.1016/j.tetasy.2003.12.018

  日期：2004.2

  A strategy for the synthesis of new chiral salen type ligands derived from alpha-D-glucose and alpha-D-mannose is described. The compounds were obtained by introducing appropriate functions at the C2 and C3 positions of the sugar ring. The efficiency of the complexes in the epoxidation of styrenes was also examined and shown to give good results, for example, cis-beta-methylstyrene was functionalised with ee's of up to 86%. (C) 2003 Elsevier Ltd. All rights reserved.