(3aS,4S,4aR,7aS,8S,8aS)-4,8-Bis-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole | 160636-42-0

• 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: (3aS,4S,4aR,7aS,8S,8aS)-4,8-Bis-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole
• CAS: 160636-42-0
• 化学式: C₂₆H₃₂O₆
• 分子量: 440.536
• InChiKey: GVSFMNAITONPJR-FOZARLDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,4aR,7aS,8S,8aS)-4,8-Bis-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 在 palladium on activated charcoal 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 氢气 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 110.0h， 生成 L-1,2-O-isopropylidene-4-O-benzoyl-6-O-benzyl-myo-inositol 3,5-bis(dibenzylphosphate)
  参考文献：
  名称：

  Divergent Synthesis of All Possible Optically Active Regioisomers ofMyo‐Inositol Mono‐ and Bisphosphates

  摘要：

  All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.[GRAPHICS]

  DOI：

  10.1080/07328300701540225
• 作为产物：
  描述：

  (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-bis(phenylmethoxy)-1,3-benzodioxole 在 四氧化锇 N-甲基吲哚酮 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 (3aS,4S,4aR,7aS,8S,8aS)-4,8-Bis-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole
  参考文献：
  名称：

  Divergent Synthesis of All Possible Optically Active Regioisomers ofMyo‐Inositol Mono‐ and Bisphosphates

  摘要：

  All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.[GRAPHICS]

  DOI：

  10.1080/07328300701540225

文献信息

• Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate
  作者：Adiyala Vidyasagar、Atchutarao Pathigoolla、Kana M. Sureshan

  DOI：10.1039/c3ob40789f

  日期：——

  cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection–deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization

  天然磷酸肌醇参与各种细胞信号转导过程，以及合成肌醇衍生物在催化，超分子化学，天然产物合成等方面的应用，推动了动力的发展。肌肌醇化学。六个仲羟基的存在需要合成肌醇衍生物的有效保护-去保护策略。初步保护艾滋病的重要策略肌肌醇是二缩酮化，它给出了三个二缩酮的混合物，每个二缩酮同时具有顺式和反式稠合的缩酮。重要的是具有方法学以选择性地水解两个缩酮之一或将两个酸不稳定缩酮之一转化为正交的碱不稳定保护基。通过利用反式-缩酮和顺式-缩酮之间的应变差异，我们开发了两种操作简单，高产的方法，用于肌醇的反式-缩酮（异丙基和环己二烯）的化学选择性水解/乙解，而顺式-缩酮不受干扰，使用便宜且易于制备的H 2 SO 4-二氧化硅作为催化剂。同样，碳水化合物和无环多元醇的末端缩酮部分可以被选择性地水解/乙酰水解，而保留内部的缩酮完整。指某东西的用途甲醇 作为溶剂会导致化学选择性醇解，但使用DCM和 醋酸酐导致化学选择性乙酰分解。应用这种方法，短合成d
• Syntheses of d- and l-myo-Inositol 1,2,4,5-tetrakisphosphate and stereoselectivity of the I(1,4,5)P3 receptor binding
  作者：Sung-Kee Chung、Boo-Gyo Shin、Young-Tae Chang、Byung-Chang Suh、Kyong-Tai Kim

  DOI：10.1016/s0960-894x(98)00081-x

  日期：1998.3

  D- and L-myo-Inositol 1,2,4,5-tetrakisphosphate [D- & L-I(1,2,4,5)P4], which are analogues of D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P3], a calcium mobilizing second messenger, were synthesized via resolution of the camphanate ester of a myo-inositol derivative, and the binding affinities to I(1,4,5)P3 receptor were measured.

  D-和L-肌醇1,2,4,5-四磷酸[D-和LI（1,2,4,5）P4]，它们是D-肌醇1,4,5-三磷酸酯的类似物通过分解肌醇衍生物的樟脑酸酯合成了一种动员钙的第二信使[DI（1,4,5）P3]，并测定了与I（1,4,5）P3受体的结合亲和力。
• The synthesis and resolution of (±)-1,4-diO-benzyl-2,3-O-isopropylidene-myo-inositol
  作者：Trupti Desai、Jill Gigg、Roy Gigg、Eloísa Martín-Zamora、Nathalie Schnetz

  DOI：10.1016/0008-6215(94)84081-4

  日期：1994.5

  Abstract An improved procedure for the preparation of 1,2-O-isopropylidene-myo-inositol is described. Racemic 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol was prepared by tinmediated benzylation of 1,2-O-isopropylidene-myo-inositol and resolved readily by crystallisation of the ω-camphanates. The use of the chiral 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositols as intermediates for the preparation

  摘要描述了一种制备1,2-O-异亚丙基-肌醇的改进方法。外消旋的1，4-二-O-苄基-2，3-O-异亚丙基-肌醇通过锡介导的1，2-O-异亚丙基-肌醇的苄基化制备，并容易通过ω-樟脑酸酯的结晶而拆分。研究了手性1,4-二-O-苄基-2,3-O-异亚丙基-肌醇的中间体作为制备肌醇其他手性衍生物的中间体。
• STEPANOV, A. E.;RUNOVA, O. B.;KRYLOVA, V. N.;USMANOVA, M. M.;SHVETS, V. I+, MOSK. IN-T. TONK. XIM. TEXNOL., M.,(1988) 10 S., ONIITEHXIM G. CHERKASSY,+
  作者：STEPANOV, A. E.、RUNOVA, O. B.、KRYLOVA, V. N.、USMANOVA, M. M.、SHVETS, V. I+

  DOI：——

  日期：——