1,2-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose | 224317-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose
• 英文别名: 3-O-(3'-methyl-2'-butenyl)-1,2-O-isopropylidene-α-D-glucofuranose；(1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(3-methylbut-2-enoxy)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 224317-44-6
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: MZCDJPYHWQRDNE-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  1,2-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose 在 sodium periodate 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成 1,2-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-xylopentadialdo-1,4-furanose
  参考文献：
  名称：

  3- O-烯丙基碳水酮硝酮环加成（3-OACNC）合成手性氧杂环丁烷和吡喃

  摘要：

  3- ø从3- -Allylcarbohydrate硝酮环加成（3- OACNC）布置吡喃和氧杂环庚烷衍生物ø -烯丙基己糖ñ -苄基硝酮和3- ö烯丙基呋喃-5-醛ñ -苄基/甲基硝酮。发现3-OACNC的区域选择性取决于以下因素（a）硝酮的结构性质（b）碳水化合物主链在3-C处的取代和立体化学（c）在O末端的取代-烯丙基部分。从特定组的己糖硝酮和相应的呋喃糖苷硝酮获得的氧杂环丁烷或吡喃通过降解转化为对映体环状醚。在3- O-烯丙基碳水合物衍生的肟的分子内肟环烯烃加成反应（IOOC ）中形成环氧丙烷和吡喃的混合物。

  DOI：

  10.1016/s0040-4020(03)00634-3
• 作为产物：
  描述：

  1-氯-3-甲基-2-丁烯 在 硫酸 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1,2-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles

  摘要：

  Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution H-1 and C-13 NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00258-6

文献信息

• Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)
  作者：Ashoke Bhattacharjee、Seema Datta、Partha Chattopadhyay、Nanda Ghoshal、Asish P Kundu、Arani Pal、Ranjan Mukhopadhyay、Sandip Chowdhury、Anup Bhattacharjya、Amarendra Patra

  DOI：10.1016/s0040-4020(03)00634-3

  日期：2003.6

  3-O-Allylcarbohydrate nitrone cycloaddition (3-OACNC) furnished pyran and oxepane derivatives from 3-O-allyl hexose N-benzyl nitrones and 3-O-allyl furanoside-5-aldehyde N-benzyl/methyl nitrones. The regioselectivity of 3-OACNC was found to depend on the following factors (a) the structural nature of the nitrone (b) substitution and stereochemistry at 3-C of the carbohydrate backbone (c) substitution

  3- ø从3- -Allylcarbohydrate硝酮环加成（3- OACNC）布置吡喃和氧杂环庚烷衍生物ø -烯丙基己糖ñ -苄基硝酮和3- ö烯丙基呋喃-5-醛ñ -苄基/甲基硝酮。发现3-OACNC的区域选择性取决于以下因素（a）硝酮的结构性质（b）碳水化合物主链在3-C处的取代和立体化学（c）在O末端的取代-烯丙基部分。从特定组的己糖硝酮和相应的呋喃糖苷硝酮获得的氧杂环丁烷或吡喃通过降解转化为对映体环状醚。在3- O-烯丙基碳水合物衍生的肟的分子内肟环烯烃加成反应（IOOC ）中形成环氧丙烷和吡喃的混合物。
• Synthesis of a new isoxazolidine from diacetone glucose
  作者：G.V.M. Sharma、I.Srinivas Reddy、V.Goverdhan Reddy、A.V.Rama Rao

  DOI：10.1016/s0957-4166(99)00008-7

  日期：1999.1

  The synthesis of a new furo-pyran-based isoxazolidine, making use of an intramolecular oxime-olefin cycloaddition (IOOC) reaction, is reported here, starting from diacetone glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of Chiral Oxepanes and Pyrans through Intramolecular Nitrone Cycloaddition in Organized Aqueous Media
  作者：Amrita Chatterjee、Pranab K. Bhattacharya

  DOI：10.1021/jo051414j

  日期：2006.1.1

  A highly stereoselective surfactant-catalyzed intramolecular nitrone (formed by dehydration in water) cycloaddition in aqueous media leading to exclusive formation of a single isomer is reported. Either oxepane or pyran is formed from 3-O-allyl furanoside derivatives, which constitute the framework of a large number of biologically active compounds. Therefore, the environmentally friendly, efficient

  据报道，在水性介质中高度立体选择性的表面活性剂催化的分子内硝酮（通过在水中脱水形成）环加成导致独家形成单个异构体。环氧丙烷或吡喃由3- O-烯丙基呋喃糖苷衍生物形成，其构成大量生物活性化合物的框架。因此，这些手性中间体的环保，有效和高度立体选择性的合成仍然是有意义的追求。
• Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles
  作者：Mirta L Fascio、Angel Alvarez-Larena、Norma B D'Accorso

  DOI：10.1016/s0008-6215(02)00258-6

  日期：2002.11

  Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution H-1 and C-13 NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.