(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde | 121845-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde
• 英文别名: 1-(2,3-O-Isopropylidene-β-D-ribo-pentodialdo-1,4-furanosyl)-3-(4-methoxybenzyl)uracil；(3aR,4R,6S,6aS)-4-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 121845-98-5
• 化学式: C₂₀H₂₂N₂O₇
• 分子量: 402.404
• InChiKey: NVXWWUGXENBWQX-VDHUWJSZSA-N

物化性质

• 沸点：
  562.1±60.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-((R)-1-{(1S,2S)-2-[(2S,5R,6S)-5-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-1,4-dimethyl-3-oxo-[1,4]diazepan-2-yl]-2-hydroxy-1-hydroxymethyl-ethoxy}-2-hydroxy-ethyl)-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of the diazepanone-nucleoside portion of liposidomycins by aldol reaction of the enolate of diazepanone with a nucleoside 5′-aldehyde

  摘要：

  The diazepanone-nucleoside part of liposidomycins has been synthesized by the aldol reaction between the enolate of a stereochemically defined diazepanone and a uridine 5'-aldehyde. The configurations of two new stereocenters in the aldol product have been assigned on the basis of the H-1 NMR coupling constants and NOE of its derivative. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00366-8
• 作为产物：
  描述：

  2’,3’邻异亚丙基尿苷 在 吡啶 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 8.25h， 生成 (3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde
  参考文献：
  名称：

  衣霉素差异保护亚基的全合成立体选择性途径

  摘要：

  La cyclocondensation d'un β-D-allo-heptodialdo-1,4 furanosyl-1 uracile issu de l'O-isopropylidene-2,3 uridine et d'un butadiene-1,3 donne un L-allo-α-D -galacto-undecodialdopyranose-1,5furanose-8,11yl 尿嘧啶。Une seconde unite d'un acetamido-2 glupyranose est egalement synthetisee。Ceci constitue unesynthese totale des intermediaires de Suami

  DOI：

  10.1021/ja00197a047

文献信息

• Acid and base stable diphenylmethanol derivatives and methods of use
  申请人：Kurosu Michio

  公开号：US20080200719A1

  公开（公告）日：2008-08-21

  The invention provides compounds that are useful as linkers for solid phase synthesis and as protecting groups, and methods for producing and using the same.

  这项发明提供了作为固相合成连接剂和保护基的化合物，以及生产和使用这些化合物的方法。
• Synthesis of sulfone-based nucleotide isosteres: identification of CMP-sialic acid synthetase inhibitors
  作者：Jessica H. Wong、Urvashi Sahni、Yanhong Li、Xi Chen、Jacquelyn Gervay-Hague

  DOI：10.1039/b819155g

  日期：——

  A modular replacement approach to the synthesis of sulfo-nucleotide analogs prepared from condensation of nucleoside aldehydes with bis phosphonate Horner-Wadsworth-Emmons reagents is disclosed. These analogs were shown to be inhibitors of Neisseria meningitidis CSS (NmCSS), which is a key enzyme in the biosynthesis of the capsular polysaccharides required for bacterial infection.

  一种模块化替代方法用于合成由核苷醛与双磷酸酯Horner-Wadsworth-Emmons试剂缩合制备的磺酸核苷类似物。研究表明，这些类似物是脑膜炎奈瑟氏菌CSS（NmCSS）的抑制剂，该酶在细菌感染所需的荚膜多糖的生物合成中起关键作用。
• Synthetic studies on nucleoside-type muraymycins antibiotics based on the use of sulfur ylides. Synthesis of bioactive 5′-epimuraymycin analogues
  作者：Francisco Sarabia、Laura Martín-Ortiz

  DOI：10.1016/j.tet.2005.09.086

  日期：2005.12

  A new synthetic approach to the 5-epimers of muraymycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy amides obtained via the reaction of sulfur ylides with the uridyl aldehyde derivatives 16, 29 and 30, followed by a subsequent oxirane ring opening reaction with diamines. This new strategy offers an excellent opportunity for the preparation of muraymycin

  一种新的合成方法，以muraymycins的5差向异构体，复杂的核苷类抗生素家族，报道基于经由硫叶立德与尿苷酰醛衍生物的反应得到的环氧酰胺的合成16，29和30，随后随后的环氧乙烷与二胺的开环反应。这一新策略为制备具有生物学意义的穆雷霉素类似物提供了极好的机会。实际上，生物学研究表明，这些5'-表位分子在生物学上与天然抗生素一样有效，除了代表着一条趋向于天然同源物的趋同而灵活的途径外。
• A Convergent Synthetic Approach to the Nucleoside-Type Liposidomycin Antibiotics
  作者：Francisco Sarabia、Laura Martín-Ortiz、F. Jorge López-Herrera

  DOI：10.1021/ol0355074

  日期：2003.10.1

  [reaction: see text] A synthetic approach toward the liposidomycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy-amides derived from the reaction of sulfur ylides with the uridyl aldehyde derivative 6. To this end, the epoxy-amide derivative of indoline 14 was stereoselectively prepared and, after treatment with DDQ, transformed into the corresponding

  [反应：见正文]据报道，合成脂苷霉素是一种复杂的核苷类抗生素家族，其合成方法是基于由硫酰化物与尿苷醛衍生物6的反应衍生的环氧酰胺的合成。为此，立体选择性制备吲哚啉14的环氧酰胺衍生物，并用DDQ处理后，转化为相应的N-吲哚环氧酰胺15。吲哚15通过反应可容易地进入脂质体中与二氮杂酮核心有关的各种结构与各种胺。
• Some novel nucleoside rearrangements effected by (diethylamino)sulphur trifluoride: synthesis and antiviral properties of some fluorine-containing 3′-azido-3′-deoxythymidine derivatives
  作者：Anne E. Lloyd、Paul L. Coe、Richard T. Walker、Oliver W. Howarth

  DOI：10.1016/s0022-1139(00)80089-5

  日期：1993.6

  The reaction of pyrimidine nucleoside 5′-aldehydes with (diethylamino)sulphur trifluoride(DAST) to produce 5′-deoxy-5′,5′-difluoronucleosides is reported. The preferred reactionis the production of the O2,5′-anhydro-5′-fluoronucleoside. If this is prevented by substitutionat 04 or N-3 then, in the former case, either DAST no longer reacts or underdrastic conditions the C(1′)N(1) bond breaks and the

  报道了嘧啶核苷5'-醛与（二乙基氨基）三氟化硫（DAST）反应生成5'-脱氧-5'，5'-二氟核苷。优选reactionis生产的O 2，5'-脱水-5'-氟核苷。如果通过在0 4或N-3处取代来防止这种情况，那么在前一种情况下，DAST不再反应或在剧烈条件下C（1'）N（1）键断裂，杂环碱基仍被C-5'连接→O 2糖基氟化物。在后一种情况下，2'，3'-O-异丙基亚氨基尿苷的5'-醛为5'-脱氧-5'，5'-二氟化合物作为唯一可识别的产物。以AZT的5'-醛（在N-3处适当保护）为起始原料，用DAST处理可生成糖基氟和其5'-脱氧-5'，5'-二氟AZT衍生物的非对映异构体混合物，其中3'可以分离出-叠氮基-3'，5'-二脱氧氧基-5'，5'-二氟胸苷。该化合物无毒，对高达100μM的1型人类免疫缺陷病毒（HIV-1）也没有任何活性。