1,2,3,4,6-penta-O-benzyl-D-chiro-inositol | 215869-70-8

• 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: 1,2,3,4,6-penta-O-benzyl-D-chiro-inositol
• CAS: 215869-70-8
• 化学式: C₄₁H₄₂O₆
• 分子量: 630.781
• InChiKey: PLKAJAVHVAUNLR-YAPCWYIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-benzyl-D-chiro-inositol 在 钯 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， -78.0 ℃ 、275.79 kPa 条件下， 反应 30.17h， 生成 D-galactopyranosyl-α-(1->2)-D-chiro-inositol
  参考文献：
  名称：

  Synthesis of a jojoba bean disaccharide

  摘要：

  A synthesis of the disaccharide recently isolated from jojoba beans, 2-O-alpha-D-galactopyranosyl-D-chiro-inositol, has been achieved. The suitably protected chiro-inositol unit was prepared by an enantiospecific synthesis from L-xylose utilizing SmI2-mediated pinacol coupling as a key step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00168-2
• 作为产物：
  描述：

  3,4,5,6-tetra-O-benzyl-D-chiro-inositol 在 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 14.25h， 生成 1,2,3,4,6-penta-O-benzyl-D-chiro-inositol
  参考文献：
  名称：

  Synthesis of a jojoba bean disaccharide

  摘要：

  A synthesis of the disaccharide recently isolated from jojoba beans, 2-O-alpha-D-galactopyranosyl-D-chiro-inositol, has been achieved. The suitably protected chiro-inositol unit was prepared by an enantiospecific synthesis from L-xylose utilizing SmI2-mediated pinacol coupling as a key step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00168-2

文献信息

• Synthesis of galactosaminyl d-chiro-inositols
  作者：Georgia Marnera、Marc d’Alarcao

  DOI：10.1016/j.carres.2006.03.031

  日期：2006.7

  All six isomeric D-galactosaminopyranosyl-D-chiro-inositols have been prepared by glycosylation of appropriate penta-O-benzyl-D-chiro-inositols. The three requisite protected D-chiro-inositols were prepared by SmI2-promoted pinacol coupling of dialdehydes derived ultimately from L-arabinose.

  通过适当的五-O-苄基-D-手性肌醇的糖基化制备了所有六个异构体D-半乳糖氨基吡喃糖基-D-手性肌醇。通过SmI2促进最终衍生自L-阿拉伯糖的二醛的频哪醇偶联制备三种必需的受保护的D-手性肌醇。
• Stereoselective α-glycosylation of C(6)-hydroxyl myo-inositols via nickel catalysis—application to the synthesis of GPI anchor pseudo-oligosaccharides
  作者：Matthew S. McConnell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1016/j.carres.2013.09.006

  日期：2013.11

  Glycosylphosphatidyl inositol (GPI) anchors play a key role in many eukaryotic biological pathways. Stereoselective synthesis of GPI anchor analogues have proven to be critical for probing the biosynthesis, structure, and biological properties of these compounds. Challenges that have emerged from these efforts include the preparation of the selectively protected myo-inositol building blocks and the stereoselective construction of glucosamine alpha-linked myo-inositol containing pseudodisaccharide units. Herein, we describe the effectiveness of the cationic nickel(II) catalyst, Ni(4-F-PhCN)(4)(OTf)(2), at promoting selective formation of 1,2-cis-2-amino glycosidic bonds between the C(2)-N-substituted benzylideneamino trihaloacetimidate donors and C(6)-hydroxyl myo-inositol acceptors. This catalytic coupling process allows rapid access to pseudosaccharides of GPI anchors in good yields and with excellent levels of a-selectivity (alpha:beta = 10:1-20:1). In stark contrast, activation of trichloroacetimidate donors containing the C(2)-N-substituted benzylidene group with TMSOTf and BF3.OEt2 provided the desired pseudodisaccharides as a 1: 1 mixture of alpha- and beta-isomers. (C) 2013 Elsevier Ltd. All rights reserved.