1,4-anhydro-3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol | 194672-69-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,4-anhydro-3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol
• 英文别名: tert-butyldiphenyl(((2R,3S)-3-((trimethylsilyl)oxy)-2,3-dihydrofuran-2-yl)methoxy)silane；tert-butyl-[[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydrofuran-2-yl]methoxy]-diphenylsilane
• CAS: 194672-69-0
• 化学式: C₂₇H₄₀O₃Si₂
• 分子量: 468.784
• InChiKey: TXETYAGBFKDVJP-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯基氯化硒 、 1,4-anhydro-3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol 、 2,4-二(三甲硅氧基)嘧啶 在 silver trifluoromethanesulfonate 作用下， 生成 、 、
  参考文献：
  名称：

  使用亲电子硒试剂从糖类合成2'-脱氧-2'-苯基硒烯基-呋喃糖基核苷。转化为2'-脱氧核苷

  摘要：

  已经使用硒试剂从糖中立体选择性地合成了2'-脱氧-2'-苯基硒烯基-呋喃糖基核苷，并通过氢化三丁基锡处理将其转化为2'-脱氧核苷。影响反应的立体选择性的一些因素是3位的立体化学，保护基团的性质，苯基硒烯基试剂和溶剂。

  DOI：

  10.1016/s0040-4020(97)00697-2
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 咪唑 、 硫酸氢铵 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1,4-anhydro-3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol
  参考文献：
  名称：

  Facile Preparation of Protected Furanoid Glycals from Thymidine

  摘要：

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.

  DOI：

  10.1021/jo970947s

文献信息

• Organocatalytic Conversion of Nucleosides to Furanoid Glycals
  作者：Edna Mao、Cheol K. Chung、Yining Ji、Yu-hong Lam、Peter E. Maligres

  DOI：10.1021/acs.joc.1c00555

  日期：2021.6.4

  2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides allowing the elimination of the nucleobase giving the corresponding glycal. These mild conditions were demonstrated in the syntheses of glycals with various substitution patterns while minimizing the formation of undesired byproducts

  已经发现了一类对将 2'-脱氧核苷转化为呋喃糖苷具有高活性的有机催化剂。这些磷酰亚胺(Ph 2 PS) 2 NH 和 (Ph 2 PSe) 2 NH 显示出可有效介导 2'-脱氧核苷的全甲硅烷基化，从而消除核碱基，产生相应的糖基。这些温和的条件在具有各种取代模式的糖醛的合成中得到了证明，同时最大限度地减少了不需要的副产物的形成并扩大了该方法的范围。
• Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl–carbohydrate derivatives
  作者：Fernando Bravo、Mohamed Kassou、Yolanda Dı́az、Sergio Castillón

  DOI：10.1016/s0008-6215(01)00256-7

  日期：2001.11

  Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions ((BuOOH)-Bu-i, Ti((OPr)-Pr-i)(4), (Et2PrN)-Pr-i). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF3. Et2O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization. (C) 2001 Published by Elsevier Science Ltd.