1,4-anhydro-3,5-di-O-(tert-butyldiphenyl)silyl-2-deoxy-D-erythro-pent-1-enitol | 105930-84-5

• 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-3,5-di-O-(tert-butyldiphenyl)silyl-2-deoxy-D-erythro-pent-1-enitol
• 英文别名: tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-2,3-dihydrofuran-2-yl)methoxy)diphenylsilane；tert-butyl-[[(2R,3S)-3-[tert-butyl(diphenyl)silyl]oxy-2,3-dihydrofuran-2-yl]methoxy]-diphenylsilane
• CAS: 105930-84-5
• 化学式: C₃₇H₄₄O₃Si₂
• 分子量: 592.926
• InChiKey: XEISMEXLWVDBML-OIDHKYIRSA-N

物化性质

• 沸点：
  596.7±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1,4-anhydro-3,5-di-O-(tert-butyldiphenyl)silyl-2-deoxy-D-erythro-pent-1-enitol 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 生成 dibenzyl 1-((2S,3S,4S,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methoxytetrahydrofuran-3-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  [4 + 2] Cycloaddition of azodicarboxylate and glycals: a novel and simple method for the preparation of 2-amino-2-deoxy carbohydrates

  摘要：

  DOI：

  10.1021/ja00235a050
• 作为产物：
  描述：

  D-(+)-核糖酸-gamma-内酯 在 咪唑 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 1,4-anhydro-3,5-di-O-(tert-butyldiphenyl)silyl-2-deoxy-D-erythro-pent-1-enitol
  参考文献：
  名称：

  A Facile, Multigram Synthesis of Ribofuranoid Glycals

  摘要：

  DOI：

  10.1021/jo951376b

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。
• An efficient and stereospecific synthesis of novel pyrazine cnucleosides
  作者：Jiong J. Chen、John A. Walker、Weimin Liu、Dean S. Wise、Leroy B. Townsend

  DOI：10.1016/0040-4039(95)01826-4

  日期：1995.11

  A novel 2′deoxyβDribofuranosyl pyrazine Cnucleoside (6) was synthesized via a Stereospecific palladium(0)mediated crosscoupling reaction. The βconfiguration of this nucleoside was established by NOE analysis and the formation of a 5,5′anhydro nucleoside 5. The compound 4a, obtained via the crosscoupling reaction and selective deprotection, is a versatile intermediate for the preparation of other pyrazine

  通过立体定向钯（0）介导的交叉偶联反应合成了新型的2'-脱氧β-呋喃呋喃糖基吡嗪核苷（6）。通过NOE分析和5,5'脱水脱水核苷5的形成，确定了该核苷的β构型。通过交叉偶联反应和选择性脱保护得到的化合物4a是用于制备其他吡嗪核苷类似物的通用中间体
• Stereocontrolled Synthesis of Aryl C-Nucleosides under Ambient Conditions
  作者：Rui Xie、Jing Xu、Haolin Shi、Chenyu Xiao、Nengzhong Wang、Nianyu Huang、Hui Yao

  DOI：10.1021/acs.orglett.4c01664

  日期：2024.6.21

  A stereocontrolled synthesis of an aryl C-nucleoside has been developed using D-ribals and arylboronic acids catalyzed by palladium without additional ligands in common solvents under an open-air atmosphere at room temperature. This protocol features very mild conditions, simplicity in operation, exclusive β-stereoselectivity, broad substrate scopes, and good compatibility with reactive amino and hydroxyl

  已经开发出一种芳基C-核苷的立体控制合成方法，使用钯催化的 D-ribals 和芳基硼酸，无需额外的配体，在普通溶剂中，在室温下的露天气氛下进行。该方案条件温和，操作简单，具有独特的β-立体选择性，底物范围广泛，与反应性氨基和羟基相容性良好。不饱和C-核苷的功能化和天然产物/药物的后期糖基化证明了该策略的高度实用性。
• 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.
• Facile Preparation of Protected Furanoid Glycals from Thymidine
  作者：Melissa A. Cameron、Sarah B. Cush、Robert P. Hammer

  DOI：10.1021/jo970947s

  日期：1997.12.1

  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%.