1L-1-O-benzyl-myo-inositol | 68738-30-7

• 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: 1L-1-O-benzyl-myo-inositol
• 英文别名: 1-O-benzyl-D-myo-inositol；3-O-benzyl-D-myo-inositol；3-O-Benzyl-sn-myoinositol；1-o-Benzyl-myo-inositol
• CAS: 68738-30-7
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: RWDNROPIZFGEAU-QPHKQPEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1L-1-O-benzyl-myo-inositol 、 碘甲烷 在 dimsyl sodium 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 ((1S,2S,3R,4S,5S,6S)-2,3,4,5,6-Pentamethoxy-cyclohexyloxymethyl)-benzene
  参考文献：
  名称：

  肌醇的一些苄基和甲基醚的合成

  摘要：

  摘要从相应的手性单-O-制备了1,2,4,5,6-和1,2,3,4,5-五-O-甲基-肌醇的1 d和1 d形式。苄基衍生物。还描述了1-，2-，4-和5-O-苄基-肌醇的非手性衍生物以及非手性1,2,4,5,6-和1,3,4,5的方便制备方法， 6-肌醇通过亚苄基衍生物的选择性苄基化和亚苄基乙缩醛的还原性裂解而形成。

  DOI：

  10.1016/s0008-6215(00)90816-4
• 作为产物：
  描述：

  2,3:5,6-二-O-亚环己基1-O-(苯基甲基)-D-肌醇 在 溶剂黄146 作用下， 反应 1.0h， 生成 1L-1-O-benzyl-myo-inositol
  参考文献：
  名称：

  Synthesis of mycothiol, 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol, principal low molecular mass thiol in the actinomycetes

  摘要：

  Members of the actinomycetes produce 1D-1-O-(2-[N-acetyl-L-cysteinyl]amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol or mycothiol 1 as principal low molecular mass thiol, Chemical synthesis of a biosynthetic precursor of mycothiol, the pseudodisaccharide 1D-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 was achieved by the following steps: (1) Enantioselcctive synthesis gave the glycosyl acceptors (-)-2,3,4,5,6-penta-O-acetyl-D-myo-inositol D-7 and the corresponding L-isomer L-7. (2) Condensation of D-7 and L-7 with the glycosyl donor 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-alpha-D-glucopyranosylbromide afforded the corresponding alpha and beta anomeric products, which could be resolved by silica gel chromatography, (3) Deprotection of these by hydrolysis using an anion exchange resin gave 1D- and 1L-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 and 15 and the corresponding beta-coupled anomers 14 and 16. Only 13, and to a much lesser extent 15, were used by enzymes present in an ammonium sulphate fraction of a cellfree extract of Mycobacterium smegmatis for the enzymatic synthesis of mycothiol. In the absence of acetyl-SCoA, the immediate biosynthetic precursor of 1, desacetylmycothiol, was the major product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00383-2

文献信息

• Design and synthesis of biotinylated inositol phosphates relevant to the biotin–avidin techniques
  作者：Kensaku Anraku、Teruhiko Inoue、Kenji Sugimoto、Takashi Morii、Yasuo Mori、Yoshinari Okamoto、Masami Otsuka

  DOI：10.1039/b719938d

  日期：——

  Six bifunctional molecules containing biotin and various inositol phosphates were synthesized. These compounds were designed on the basis of X-ray structures of the complexes of D-myo-inositol 1,4,5-triphosphates (IP3) and phospholipase C δ pleckstrin homology domain (PLCδ PH) considering the application to the biotin–avidin techniques. The building blocks of the inositol moiety were synthesized starting with optically resolved myo-inositol derivatives and assembled to the biotin linker through a phosphate linkage.

  合成了六种含有生物素和各种肌醇磷酸盐的双功能分子。这些化合物的设计基于D-myo-肌醇1,4,5-三磷酸（IP3）与磷脂酶C δ pleckstrin同源域（PLCδ PH）复合物的X射线结构，考虑到生物素-抗生物素技术的应用。肌醇部分的构建块是从光学分解的myo-肌醇衍生物开始合成的，并通过磷酸链接组装到生物素链接器上。
• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 2): Via Nonsymmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400918

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  一种实用的路线的制备描述肌醇肌醇磷酸盐。可以通过对乙酰氨基乙酸二硬脂醇关键中间体的酶促拆分，从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可通过破坏Conduritol B衍生物的C 2对称性而获得。各种各样的肌肌醇磷酸盐可以通过组合与这个新的非对称的方法先前报道的对称方法来合成。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）
• Process for the preparation of myoinositol derivatives
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0262227B1

  公开（公告）日：1993-01-20
• INOSITOL PHOSPHOGLYCAN DERIVATIVES AND THEIR MEDICAL USES
  申请人：Rodaris Pharmaceuticals Limited

  公开号：EP1409501A1

  公开（公告）日：2004-04-21
• INOSITOL-BASED IMMUNOTHERAPIES
  申请人：NormOxys, Inc.

  公开号：EP3787634A1

  公开（公告）日：2021-03-10