2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose | 163040-86-6

• 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: 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose
• 英文别名: (2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxane-2-carbaldehyde
• CAS: 163040-86-6
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: NMURRMJXWKZQRK-ABDYMBPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 四甲基乙二胺 、 氨 、 三正丁基氢锡 、 三乙胺 、 magnesium bromide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 苯 为溶剂， 反应 12.5h， 生成 (2R,3R,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019
• 作为产物：
  描述：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 正丁基锂 、 samarium diiodide 、 乙二醇 、 三乙胺 、 pyridinium chlorochromate 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 45.26h， 生成 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose
  参考文献：
  名称：

  立体选择性合成α-和β-1- C-岩藻糖基醛及其在具有生物意义的C-岩藻糖苷组装中的用途

  摘要：

  的有效合成ö经由噻唑除了三-benzylated标题糖醛衍生物ö苄基升-fuconolactone接着将得到的thiazolylketose和噻唑甲酰基到变换进行说明的高立体选择性的脱氧。维蒂希这些醛与半乳糖和D-吡喃葡萄糖6-膦和减少的烯化所得的烯烃，得到α-和β连接的（1→6） -升- Ç -fucosyl二糖，即，β-升- Ç -Fuc-（1 →6）-α- d -Gal，α-升- ç -Fuc-（1→6）-α- d -Gal，和α-升-C -Fuc-（1→6）-α- d- Glc。将上述C-岩藻糖基醛的α-端基异构体转化为C-岩藻糖基甲基三苯基碘化碘，用BuLi处理后，从中生成相应的C-岩藻糖基亚甲基phosphor烷。此正膦与加纳醛反应（Ñ -Boc d -serinal丙酮化合物）和它的一碳同系物更高，得到烯烃从得到恶唑烷环，其减少和揭晓了甘氨组Ç -fucosylα氨基酸，即α-升-连接ç

  DOI：

  10.1021/jo049406a

文献信息

• Preferred Conformations of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II
  作者：Alexander Wei、Arnaud Haudrechy、Catharine Audin、Hyuk-Sang Jun、Nathalie Haudrechy-Bretel、Yoshito Kishi

  DOI：10.1021/jo00112a040

  日期：1995.4

  The syntheses of C-trisaccharides 1-4, carbon analogs of the human blood group determinant II-type II, have been achieved in a flexible and efficient manner. Vicinal coupling constants in the H-1 NMR spectrum provide experimental evidence that each of the four compounds 1-4 possesses a unique solution conformation, in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the influence of 1,3-diaxial like interactions about the C-aglyconic bond.
• Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides
  作者：Toru Haneda、Peter G. Goekjian、Sung H. Kim、Yoshito Kishi

  DOI：10.1021/jo00028a019

  日期：1992.1

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.
• Stereoselective Synthesis of α- and β-<scp>l</scp>-<i>C</i>-Fucosyl Aldehydes and Their Utility in the Assembly of <i>C</i>-Fucosides of Biological Relevance
  作者：Alessandro Dondoni、Nicola Catozzi、Alberto Marra

  DOI：10.1021/jo049406a

  日期：2004.7.1

  C-fucosyl serines and C-fucosyl asparagines. As a final test of the synthetic utility of the title aldehydes, the β-anomer was employed as starting material in the stereoselective synthesis of both R- and S-epimer l-C-fucosyl phenylhydroxy acetates. One epimer was obtained by reaction of the sugar aldehyde with phenylmagnesium bromide, oxidation of the resulting alcohol to ketone, addition of 2-lithiothiazole

  的有效合成ö经由噻唑除了三-benzylated标题糖醛衍生物ö苄基升-fuconolactone接着将得到的thiazolylketose和噻唑甲酰基到变换进行说明的高立体选择性的脱氧。维蒂希这些醛与半乳糖和D-吡喃葡萄糖6-膦和减少的烯化所得的烯烃，得到α-和β连接的（1→6） -升- Ç -fucosyl二糖，即，β-升- Ç -Fuc-（1 →6）-α- d -Gal，α-升- ç -Fuc-（1→6）-α- d -Gal，和α-升-C -Fuc-（1→6）-α- d- Glc。将上述C-岩藻糖基醛的α-端基异构体转化为C-岩藻糖基甲基三苯基碘化碘，用BuLi处理后，从中生成相应的C-岩藻糖基亚甲基phosphor烷。此正膦与加纳醛反应（Ñ -Boc d -serinal丙酮化合物）和它的一碳同系物更高，得到烯烃从得到恶唑烷环，其减少和揭晓了甘氨组Ç -fucosylα氨基酸，即α-升-连接ç