1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol | 111651-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol
• 英文别名: 1,6-diazido-1,6-dideoxy-3,4-O-isopropylidene-L-iditol；(1S)-2-azido-1-[(4R,5R)-5-[(1S)-2-azido-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 111651-40-2
• 化学式: C₉H₁₆N₆O₄
• 分子量: 272.264
• InChiKey: HTVGXLIEHIIWQN-RULNZFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  156.44
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol 在 palladium on activated charcoal 氨 、 氢气 、 sodium 、 sodium hydride 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 (5S,6R,7R,8S)-5,6,7,8-tetrahydroxy-6,7-methylethylidene-2-imino-1,3-diazonane
  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
• 作为产物：
  描述：

  3,4-O-methylethylidene-D-mannitol 在 sodium azide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol
  参考文献：
  名称：

  Synthesis of C2-symmetric bis(cyclic isothioureas) as potent inhibitors of glycosidases

  摘要：

  Enantiopure C-2-symmetric bis(cyclic isothioureas), considered as potent inhibitors of glycosidases, have been synthesized from D-mannitol. The key step involved a mercuric-catalyzed transformation of a cyclic 1,3-thiazolidine-2-thione into a 2-N-tert-butylamino-1,3-thiazoline. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00593-6

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 (<i>R</i>) and (<i>S</i>)-α-Hydroxy-β-Amino Propionaldehydes and Propionic Acids From D-Mannitol
  作者：A. Dureault、I. Tranchepain、J. C. Depezay

  DOI：10.1055/s-1987-27979

  日期：——

  An easy method to prepare (R)- and (S)-isoserine from D-mannitol is reported. Suitably protected (R)- or (S)-α-hydroxy-β-aminopropanals are also accessible by the same route.

  报告了一种从 D-甘露醇制备 (R)- 和 (S)- 异丝氨酸的简便方法。通过同样的方法也可以制备得到适当保护的(R)-或(S)-δ-羟基δ-²-氨基丙醛。
• Synthesis of d-mannitol and l-iditol derivatives as monomers for the preparation of new regioregular AABB-type polyamides
  作者：Manuel Mancera、Isaac Roffé、Manuel Rivas、Carmen Silva、Juan A. Galbis

  DOI：10.1016/s0008-6215(02)00040-x

  日期：2002.4

  1,6-Diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-D-mannitol (and its L-iditol analogue) suitable for their utilization as monomers in the preparation of linear polyamides are described. Regio- and stereoregular polyamides of the AABB-type have been prepared by the active ester polycondensation method from these C(2) symmetric monomers and suberic and dodecanedioic acids. The resulting polyamides were

  适合用作制备线性聚酰胺的单体的1,6-二氨基-1,6-二脱氧-2,3,4,5-四-O-甲基-D-甘露醇是（及其左旋糖醇类似物）描述。通过活性酯缩聚方法，由这些C（2）对称单体以及辛二酸和十二烷二酸制备了AABB型区域和立构规整型聚酰胺。得到的聚酰胺以合理的收率（70-60％）获得，并通过元素分析和红外光谱以及1H和13C NMR光谱进行表征。它们的M（w）和M（w）/ M（n）是通过GPC相对于聚苯乙烯标准品确定的。它们都是粘性的非结晶固体。