1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose | 270923-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose
• 英文别名: (1R,5R)-3-[(R)-hydroxy-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-6,8-dioxabicyclo[3.2.1]oct-3-en-2-one
• CAS: 270923-04-1
• 化学式: C₄₁H₄₂O₉
• 分子量: 678.779
• InChiKey: DAMDSSRNXJYUBM-XEQXWUGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose 在 叔丁基过氧化氢 、 二乙胺基三氟化硫 、 水 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose 、 isolevoglucosenone 在 二乙基碘化铝 作用下， 生成 1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462

文献信息

• Syntheses of -C(1→3)-Glucopyranosides of 2- and 4-Deoxy-D-hexoses
  作者：Raynald Demange、Carine Bühlmann、Pierre Vogel

  DOI：10.1002/hlca.200390037

  日期：2003.2

  7-tetra-O-benzyl-D-glycero-D-gulo-heptose (5) gave an enone 6 that was converted with high stereoselectivity to 3-C-[(1R)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-D-arabino-hexose (1; 1 : 1 mixture of α- and β-D-pyranose), and to 3-C-[(1R)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-D-lyxo-hexose (2; 2.7 : 1.4 : 1.0 : 1.4 mixture of α-D-furanose, β-D-furanose, α-D-pyranose

  所述OshimaNozaki（ET 2 ALI）isolevoglucosenone（缩合4）与2,6-脱水3,4,5,7-四- ø -苄基-D-甘油- D-庚-heptose（5），得到烯酮6被转换高立体选择性，以3- ç - [（1 - [R）-2,6-脱水-D-甘油- D-庚-heptitol -1- ç基] -2,3-二脱氧D-阿拉伯-己糖（1 ; 1：1个混合物α -和β -D-吡喃糖），以及3- ç - [（1 - [R基）-2,6-脱水-D-甘油- D-庚-heptitol -1- Ç基] -2,3-二脱氧D-来苏-hexose（2 ; 2.7：1.4：1.0：1.4的混合物α - D-呋喃糖，β -D-呋喃糖，α -D-吡喃糖和β -D-吡喃糖）。所述OshimaNozaki（ET 2 levoglucosenone（的ALI）缩合17）与醛5，得到烯酮18，将其转变高立体选择性，以3-
• Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone
  作者：Yao-Hua Zhu、Raynald Demange、Pierre Vogel

  DOI：10.1016/s0957-4166(99)00492-9

  日期：2000.1

  Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta-D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-<i>C</i>-[(1<i>R</i>)-2,6-anhydro-1-deoxy-1-fluoro-<scp>d</scp>-<i>g</i><i>lycero</i>-<scp>d</scp>-<i>g</i><i>ulo</i>- heptitol-1-<i>C</i>-yl]-β-<scp>d</scp>-<i>g</i><i>ulo</i>-furanose:  First Example of a Monofluoromethylene-Linked <i>C</i>-Disaccharide
  作者：Jesús Jiménez-Barbero、Raynald Demange、Kurt Schenk、Pierre Vogel

  DOI：10.1021/jo0102462

  日期：2001.7.1

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.