(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 | 1219030-92-8

• 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: (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
• 英文别名: (4S)-4-[(R)-[6-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1,4-dithiin-5-yl]-phenylmethoxymethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1219030-92-8
• 化学式: C₂₆H₃₂O₅S₂
• 分子量: 488.669
• InChiKey: PBUXJHYTCMJMGL-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 3.0h， 以92%的产率得到(3-(R)-1-(benzyloxy)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-5,6-dihydro-1,4-dithiin-2-yl)methanol
  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)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](3-[(4-methoxybenzyl)oxy]methyl-5,6-dihydro-1,4-dithiin-2-yl)methanol 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以98%的产率得到(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
  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.