(1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene | 102997-58-0

• 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: (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene
• 英文别名: (3S,4R,5R)-tribenzyloxy-(6S)-hydroxycyclohexene；conduritol B；(1S,4S,5R,6R)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol
• CAS: 102997-58-0
• 化学式: C₂₇H₂₈O₄
• 分子量: 416.517
• InChiKey: FHCUPPPGVZNUCJ-GWMMUDDPSA-N

物化性质

• 熔点：
  116-119 °C
• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 在 palladium on activated charcoal 、 对甲苯磺酸 sodium hydroxide 、 R-Alpine-Hydride 、 3 A molecular sieve 、 三氟化硼乙醚 、 四丁基溴化铵 、 氢气 、 双氧水 、 sodium hydride 、 二正丁基氧化锡 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.5h， 生成 Quebrachitol, (-)-
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium hydride 、 甲基磺酰氯 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.67h， 生成 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035

文献信息

• A Novel Approach to Anellated Carbasugar Derivatives, Using Intramolecular 1,3-Dipolar Cycloaddition Reactions of Sugar-Derived Nitrones
  作者：Michael Lalk、Helmut Reinke、Klaus Peseke

  DOI：10.1002/1099-0690(200102)2001:4<759::aid-ejoc759>3.0.co;2-r

  日期：2001.2

  Intramolecular 1,3-dipolar cycloaddition of the intermediate nitrones 5 and 6 to double bonds stereoselectively yielded the benzylated anellated carbasugar derivatives 7 and 8. The disaccharide analogue 14 was synthesized similarly. Deprotection afforded the anellated carbasugars 9, 10, and 15, which were investigated as potential inhibitors of glycosidases. This paper also describes the theoretical

  中间硝基5和6到双键的分子内1，3-偶极环加成立体选择性地产生了苄基化的带烷基的羧化糖衍生物7和8。类似地合成了二糖类似物14。脱保护，得到端环carbasugars 9，10，和15，将其调查作为糖苷酶潜在抑制剂。本文还描述了分别使用自动对接程序和酶测定法对这些化合物作为不同酶的配体进行的理论和实验评估。
• Synthesis of Cyclophellitol Utilizing a Palladium Chloride Mediated-Ferrier-II Rearrangement
  作者：H. Takahashi、S. Ikegami

  DOI：10.3390/10080901

  日期：——

  Cyclophellitol and its C3-epimer have been synthesized from 5-enoglucopyranoside and 5-enomannopyranoside, respectively. The carbocyclic skeleton was constructed through a Ferrier-II reaction meditated by PdCl2.

  Cyclophellitol 及其 C3-差向异构体分别由 5-enoglucopyranoside 和 5-enomannopyranoside 合成。碳环骨架是通过 PdCl2 介导的 Ferrier-II 反应构建的。
• Synthesis of branched-chain<scp>D</scp>-myo-inositols using the [3,3]sigmatropic Claisen rearrangement
  作者：Sophie Augy-Dorey、Derek H. R. Barton、Stephen D. Géro、Béatrice Quiclet-Sire、Isabella Sagnard

  DOI：10.1039/c39930000960

  日期：——

  A new and efficient synthesis of branched-chain cyclitols and their congeners utilizing a stereospecific Claisen rearrangement is reported.

  报告了一种利用立体特异性克莱森重排反应合成新型高效支链环醇及其类似物的方法。
• Stereospecific route for the synthesis of 1,5-lactams : Synthesis of (2S,3S,4R,5R)-methyl-3,4,5-triphenylmethylenoxy-6-oxo-piperidine-2-carboxylate
  作者：Sreenivasulu Guntha、Hari Babu Mereyala

  DOI：10.1016/s0040-4039(00)76990-5

  日期：1994.7

  Synthesis of derivative 4, an oxidation product of nojirimycin, from D-glucose is described, involving, ozonolysis of 8 as key step.

  描述了由D-葡萄糖合成衍生物4（一种诺奇霉素的氧化产物），其中涉及将臭氧8分解为关键步骤。
• A Synthesis of Conduramine B and a 'Condurithiol', useful Molecules for Studying the Inhibition of &amp;beta;-Xylosidases
  作者：Matthew J. McDonough、Robert V. Stick、D. Matthew G. Tilbrook

  DOI：10.1071/c97166

  日期：——

  Conduramine B and a ‘condurithiol’, namely (1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol and (1R,2S,3R,6R)-6-sulfanylcyclohex-4-ene-1,2,3-triol, have been prepared by the thermal rearrangement of an acetimidate and a dithiocarbonate, respectively. Both the amine and the thiol are putative inhibitors of β-xylosidases and, in order to mimic the natural substrate more closely, an N- and an S-pseudo-disaccharide have been prepared.

  康杜拉明 B 和一种 "康杜硫醇"，即 (1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol 和 (1R,2S,3R,6R)-6-sulfanylcyclohex-4-ene-1,2,3-triol, 的热重排制备而成。 二硫代碳酸酯进行热重排而制备的。胺和硫醇都是推定的 为了更接近地模拟天然底物 为了更接近天然底物，一种 N 为了更接近天然底物，我们制备了一种 N-和一种 S-伪二糖。