3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol | 142285-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol
• 英文别名: (4R,5R)-4,5-bis[(1S)-1-azido-2-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 142285-65-2
• 化学式: C₂₃H₂₈N₆O₄
• 分子量: 452.513
• InChiKey: ZUALHLNDGGFBEX-FNAHDJPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol 在 Lindlar's catalyst sodium tetrahydroborate 、 sodium periodate 、 camphor-10-sulfonic acid 、 氢气 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol
  参考文献：
  名称：

  Regioselective cleavage of the bis-benzylidene acetal of d-mannitol under oxidative and reductive conditions: a new approach to C2-symmetric chiral ligands

  摘要：

  A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-D-mannitol was carried out using NBS and the resultant product was readily converted to the Q-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5-hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-D-mannitol was achieved in a highly regioselective manner using BF(3)center dot OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C-2-symmetric bis-amino alcohol derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.038
• 作为产物：
  描述：

  3,4-di-O-isopropylidene-D-mannitol 在 sodium azide 、 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.08h， 生成 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol
  参考文献：
  名称：

  Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases

  摘要：

  A series of enantiomerically pure C-2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N,N"-trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit alpha-L-fucosidase of bovin kidney (2.8 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00294-1

文献信息

• Synthesis of C₂-Symmetrical Cyclic Guanidino-Sugars from d-Mannitol
  作者：Laurence Gauzy、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1055/s-1998-3129

  日期：1998.4

  An efficient method für the synthesis of C2-symmetrical cyclic guanidino-sugars has been developed from 1,2:5,6-dianhydro-3,4-O-methylethylidene-d-mannitol or l-iditol.

  从 1,2:5,6-二氢-3,4-O-甲基亚乙基-d-甘露醇或 l-iditol 中开发出了一种合成 C2 对称环状胍基糖的高效方法。
• Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol
  作者：Devarajulu Sureshkumar、Susama Maity、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2006.08.035

  日期：2006.10

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Reddy, P. Ganapati; Pratap, T. Verabhadra; Kumar, G. D. Kishore, European Journal of Organic Chemistry, 2002, # 22, p. 3740 - 3744
  作者：Reddy, P. Ganapati、Pratap, T. Verabhadra、Kumar, G. D. Kishore、Mohanty, Subhendu K.、Baskaran, Sundarababu

  DOI：——

  日期：——
• Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases
  作者：Yves Le Merrer、Laurence Gauzy、Christine Gravier-Pelletier、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00294-1

  日期：2000.2

  A series of enantiomerically pure C-2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N,N"-trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit alpha-L-fucosidase of bovin kidney (2.8 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Regioselective cleavage of the bis-benzylidene acetal of d-mannitol under oxidative and reductive conditions: a new approach to C2-symmetric chiral ligands
  作者：Appu Aravind、Subhendu K. Mohanty、T. Veerabhadra Pratap、Sundarababu Baskaran

  DOI：10.1016/j.tetlet.2005.03.038

  日期：2005.4

  A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-D-mannitol was carried out using NBS and the resultant product was readily converted to the Q-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5-hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-D-mannitol was achieved in a highly regioselective manner using BF(3)center dot OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C-2-symmetric bis-amino alcohol derivative. (c) 2005 Elsevier Ltd. All rights reserved.