1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dibromomethylene)-α-D-glycero-D-galacto-hexitol | 946416-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dibromomethylene)-α-D-glycero-D-galacto-hexitol
• 英文别名: (1S,3R,4R,5S,6S)-7,7-dibromo-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane
• CAS: 946416-32-6
• 化学式: C₃₅H₃₄Br₂O₅
• 分子量: 694.46
• InChiKey: VDKVSRFGGUSEMA-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dibromomethylene)-α-D-glycero-D-galacto-hexitol 在 Oxone 、 sodium tetrahydroborate 、 正丁基锂 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 methyl 4,5,7-tri-O-benzyl-α-D-glycero-D-talo-septanoside
  参考文献：
  名称：

  Synthesis of Septanosides through an Oxyglycal Route

  摘要：

  A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation, and reduction. Methyl septanoside derivatives, namely, methyl alpha-D-glycero-D-talo-septanoside and methyl alpha-D-glycero-L-altro-septanoside, were synthesized in an overall yield of 35% and 46%, respectively, from the corresponding protected 2-hydroxy glycals.

  DOI：

  10.1021/jo070444e
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol 、 三溴甲烷 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 3.0h， 以81%的产率得到1,5-anhydro-2,3,4,6-tetra-O-benzyl-1,2-C-(dibromomethylene)-α-D-glycero-D-galacto-hexitol
  参考文献：
  名称：

  Synthesis of Septanosides through an Oxyglycal Route

  摘要：

  A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation, and reduction. Methyl septanoside derivatives, namely, methyl alpha-D-glycero-D-talo-septanoside and methyl alpha-D-glycero-L-altro-septanoside, were synthesized in an overall yield of 35% and 46%, respectively, from the corresponding protected 2-hydroxy glycals.

  DOI：

  10.1021/jo070444e

文献信息

• Branching out at <i>C</i>-2 of septanosides. Synthesis of 2-deoxy-2-<i>C</i>-alkyl/aryl septanosides from a bromo-oxepine
  作者：Supriya Dey、Narayanaswamy Jayaraman

  DOI：10.3762/bjoc.8.59

  日期：——

  moieties in C-C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl

  本文涉及 2-脱氧-2-C-烷基/芳基七糖苷的合成。通过使用常见的溴-氧杂环庚烷中间体合成了一系列此类 septanoside 衍生物，涉及形成 CC 键的有机金属反应。不饱和的七元七元七醇溴化乙烯或溴氧杂环庚烷，通过环丙烷衍生物的扩环方法获得，对 CC 键形成 Heck、Suzuki 和 Sonogashira 偶联反应中的几个受体部分显示出良好的反应性，从而提供 2-脱氧-2-C-烷基/芳基七糖苷。Heck 和 Sonogashira 偶联反应分别提供了 2-脱氧-2-C-烯基和 -炔基衍生物，而 Suzuki 反应提供了 2-脱氧-2-C-芳基七糖苷。2-脱氧-2-烯基衍生物的脱保护和还原得到相应的不含保护基团的2-脱氧-2-C-烷基七糖苷。本研究说明了溴-氧杂环庚烷在合成迄今未知的七糖苷中的反应性，通过与烷基和芳基取代基形成 CC 键，在 C-2 处分支。