((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol | 144732-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
• 英文别名: 3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-galacto-heptitol；3,6-anhydro-1,2,4,5-di-O-isopropylidene-D-glycero-D-galactoheptitol；[(3aS,4R,6S,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 144732-47-8；144651-34-3
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: RQJXVTDIPBQDFO-LXUNUROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 bismuth(III) chloride 、 硫酸 、 水 、 碘 、 氧气 、 sodium hydride 、 三苯基膦 、 copper(l) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 16.0h， 生成 1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione
  参考文献：
  名称：

  Synthesis of N-homobicyclic dideoxynucleoside analogues

  摘要：

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.018
• 作为产物：
  描述：

  D-甘露糖 在 硫酸 、 potassium tert-butylate 、 copper(II) sulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.5h， 生成 ((3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
  参考文献：
  名称：

  Synthesis of N-homobicyclic dideoxynucleoside analogues

  摘要：

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.018

文献信息

• Total Synthesis of (−)-Orthodiffenes A and C
  作者：Jun Liu、Yi Liu、Xing Zhang、Chaoli Zhang、Yangguang Gao、LinLin Wang、Yuguo Du

  DOI：10.1021/jo301829p

  日期：2012.11.2

  orthodiffenes A and C, including their absolute stereochemistry. The key steps of our total synthesis involved cis-fused tetrahydrofuran cyclization, one-pot deprotection–lactonization, and intramolecular benzoyl migration according to a biosynthetic hypothesis of orthodiffenes.

  （-）-正交二烯A和C的高效，简捷合成是从容易获得的手性合成子，d-甘露糖和d-乳酸乙酯分八步完成的。我们的工作证实了正二烯A和C的完整结构，包括其绝对的立体化学。根据原邻二烯的生物合成假设，我们全合成的关键步骤包括顺式融合的四氢呋喃环化，一锅脱保护-内酯化和分子内苯甲酰迁移。
• Réaction d'Ylures du soufre sur des sucres réducteurs: Application à la synthèse d'hydroxyméthyl C-glycosides.
  作者：C. Fréchou、L. Dheilly、D. Beaupère、R. Uzan、G. Demailly

  DOI：10.1016/s0040-4039(00)61191-7

  日期：1992.8

  Treatment of reducing carbohydrates with unstabilized sulfur ylides affords epoxy alcohols. When the reaction is not accompanied by elimination of a leaving group at C-3, spontaneous cyclisation occurs, and hydroxymethyl C-glycosyl compounds are obtained.
• Synthesis and antitumor activity of goniofufurone analogues
  作者：Hari Babu Mereyala、Rajendrakumar Reddy Gadikota、Maju Joe、Sudershan K. Arora、Sunanda G. Dastidar、Sudhanshu Agarwal

  DOI：10.1016/s0968-0896(99)00164-9

  日期：1999.9

  Synthesis and antitumor activity of goniofufurone analogues 15, 16, 17, 33, and 46 is reported. Key step in the synthesis is Pd (II) mediated oxidative cyclisation of vinyl-(hydroxy) furans 18, 19 to the corresponding lactols 32, 43. Cytotoxicities of 15, 16, 17, 33, and 46 tested against six human cancer cell lines are reported. Change of stereochemistry at C-5, C-6 and C-7 position of goniofufurone (1) did not enhance the cytotoxicities significantly.
• Mereyala, Hari Babu; Gadikota, Rajendrakumar Reddy; Krishnan, Ravikumar, Journal of the Chemical Society. Perkin transactions I, 1997, # 23, p. 3567 - 3571
  作者：Mereyala, Hari Babu、Gadikota, Rajendrakumar Reddy、Krishnan, Ravikumar

  DOI：——

  日期：——
• Synthesis of N-homobicyclic dideoxynucleoside analogues
  作者：N. Raghavendra Swamy、N. Suryakiran、P. Paradesi Naidu、Y. Venkateswarlu

  DOI：10.1016/j.carres.2012.01.018

  日期：2012.5

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.