(1S,8R,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene | 1219031-02-3

• 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: (1S,8R,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene
• CAS: 1219031-02-3
• 化学式: C₁₅H₁₆O₃S₂
• 分子量: 308.422
• InChiKey: DUWBUAWNXZJBOQ-ZOWXZIJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,8R,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene 在 水 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以78%的产率得到4-O-benzyl-1,6-anhydro-2,3-dideoxy-β-L-threo-hex-2-enopyranose
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k
• 作为产物：
  描述：

  (R)-(benzyloxy)[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](3-[(4-methoxybenzyl)oxy]methyl-5,6-dihydro-1,4-dithiin-2-yl)methane 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到(1S,8R,9S)-8-phenylmethoxy-11,12-dioxa-3,6-dithiatricyclo[7.2.1.02,7]dodec-2(7)-ene
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k

文献信息

• Highly Stereoselective <i>de Novo</i> Synthesis of <scp>l</scp>-Hexoses
  作者：Annalisa Guaragna、Daniele D’Alonzo、Concetta Paolella、Carmela Napolitano、Giovanni Palumbo

  DOI：10.1021/jo100077k

  日期：2010.6.4

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.