3,4,5,6-tetra-O-benzyl-D-chiro-inositol | 202798-29-6

• 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: 3,4,5,6-tetra-O-benzyl-D-chiro-inositol
• 英文别名: (1S,2R,3S,4S,5S,6R)-3,4,5,6-tetrakis(phenylmethoxy)cyclohexane-1,2-diol
• CAS: 202798-29-6
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: VQNWAWRYJQHLAV-HJBNHHNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetra-O-benzyl-D-chiro-inositol 在 钯 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 氢气 、 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 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， -78.0~25.0 ℃ 、275.79 kPa 条件下， 反应 44.42h， 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：

  (2R,3R,4R,5S)-2,3,4,5-tetrakis(phenylmethoxy)hexanedial 在 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 3,4,5,6-tetra-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

• Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction
  作者：Zhaozhong J. Jia、Lars Olsson、Bert Fraser-Reid

  DOI：10.1039/a800282g

  日期：——

  Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.

  微生物芳烃氧化或烯醇酯的费里尔反应提供了多种互补途径，极大地方便了GPI组装中肌醇构建单元（们）的制备。
• 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。
• Synthesis of New HexosaminylD- andL-chiro-Inositols Related to Putative Insulin Mediators
  作者：M. Belén Cid、Julia B. Bonilla、Francisco Alfonso、Manuel Martín-Lomas

  DOI：10.1002/ejoc.200300252

  日期：2003.9

  of tetrabenzoyl-L-chiro-inositol 2 and tetrabenzyl-D-chiro-inositol 14. Compounds XII−XV may constitute the central structural motifs of inositolphosphoglycans, which have been proposed as putative insulin mediators, and their syntheses have been designed on the basis of biosynthetic considerations. The syntheses of XII−XIII and XIV−XV involve the selective monoglycosylation of an L-chiro inositol diequatorial

  我们开发了一种高效的 HexNH2-α(1⇄3)-L-手性肌醇 (XII-XIII) 和 HexNH2-α(1⇄2)-D-手性肌醇 (XIV-XV) 的合成策略四苯甲酰-L-手性肌醇 2 和四苄基-D-手性-肌醇 14 的区域和立体选择性糖基化。基于生物合成考虑而设计。XII-XIII 和 XIV-XV 的合成分别涉及 L-手性肌醇双赤道二醇系统 (2) 和 D-手性肌醇轴向/赤道二醇系统 (14) 的选择性单糖基化。为了建立实验条件以达到最佳的反应性 - 选择性平衡，使用具有不同反应性的 D-葡萄糖和 D-半乳糖构型的 2-叠氮基-2-脱氧三氯乙酰亚胺糖基供体研究糖基化反应。获得的结果提供了实用的合成路线和新的反应-选择性数据。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• On the origin of the regioselectivity in glycosylation reactions of 1,2-diols
  作者：M. Belén Cid、Francisco Alfonso、Inés Alonso、Manuel Martín-Lomas

  DOI：10.1039/b819452a

  日期：——

  The assistance of neighboring protecting groups with different orientations in 1,2-diol acceptors and the reactivity of both reaction partners, the donor and the acceptor, have been evaluated as factors that determine the regioselectivity of glycosylation reactions. It has been established, by experimental and theoretical studies, that the regioselectivity for the glycosylation of a given OH group can be considerably increased by the presence of groups able to form a hydrogen bond with that OH group. Moreover higher regioselectivities are observed when armed donor/activated acceptor combinations are avoided.

  1,2-二醇受体中具有不同方向的相邻保护基团的协助以及反应伙伴（供体和受体）的反应性已被评估为决定糖基化反应的区域选择性的因素。通过实验和理论研究已经确定，给定OH基团的糖基化的区域选择性可以通过能够与该OH基团形成氢键的基团的存在而显着增加。此外，当避免武装供体/活化受体组合时，观察到更高的区域选择性。