(3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole | 78341-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
• 英文别名: (3aR,6S,6aS)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 78341-96-5
• 化学式: C₉H₁₅BrO₄
• 分子量: 267.12
• InChiKey: WAABJMSNMPZCDB-XDTPYFJJSA-N

物化性质

• 沸点：
  295.4±40.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 57.0h， 生成 去氧氟尿苷
  参考文献：
  名称：

  5'-脱氧-5-氟-尿素（5-DFUR）和抑制剂5'-氘代衍生物的立体立体合成5'-氘代衍生物†

  摘要：

  立体定向合成抗癌剂5'-脱氧-5-氟尿嘧啶及其5'-氘代衍生物

  DOI：

  10.1002/hlca.19820650525
• 作为产物：
  描述：

  D-吡喃核糖 在 吡啶 、 lithium bromide 作用下， 以 丁酮 为溶剂， 反应 98.0h， 生成 (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
  参考文献：
  名称：

  Synthesis of Aminocyclopentanetriol Derivatives

  摘要：

  本发明涉及有机合成领域，描述了适用于制备三唑吡咯嘧啶类化合物（如替卡格雷）的特定中间体的合成。本发明特别提供了一种制备化合物V的方法，包括：a）提供化合物IV的步骤，和b）在铜的存在下，使用活性锌还原化合物IV以得到化合物V的步骤。

  公开号：

  EP2666771A1

文献信息

• [EN] SYNTHESIS OF TRIAZOLOPYRIMIDINE COMPOUNDS<br/>[FR] SYNTHÈSE DE COMPOSÉS DE TRIAZOLOPYRIMIDINE
  申请人：LEK PHARMACEUTICALS

  公开号：WO2013092900A1

  公开（公告）日：2013-06-27

  The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

  本发明涉及有机合成领域，描述了合成特定中间体的方法，适用于制备三唑吡咯啉类化合物，如替卡格雷。
• 5'-Deoxy-5-fluorouridine
  申请人：Hoffmann-La Roche Inc.

  公开号：US04340729A1

  公开（公告）日：1982-07-20

  A process for the manufacture of 5'-deoxy-5-fluorouridine which is a potent antitumor agent. The process comprises cleaving the acyl groups from a 1-(5-deoxy-2,3-di-O-acyl-.beta.-D-ribofuranosyl)-5-fluorouracil, a novel intermediate in the process.

  一种制造5'-去氧-5-氟尿嘧啶的工艺，该化合物是一种有效的抗肿瘤剂。该工艺包括从1-(5-去氧-2,3-二-O-酰基-.beta.-D-核糖呋喃苷)-5-氟尿嘧啶中剥离酰基团，是该工艺中的一种新型中间体。
• Synthesis of Triazolopyrimidine Compounds
  申请人：Lek Pharmaceuticals d.d.

  公开号：US20140371449A1

  公开（公告）日：2014-12-18

  The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

  本发明涉及有机合成领域，并描述了合成特定中间体的方法，适用于制备三唑并嘧啶类化合物，如替卡格雷。
• 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：——

  公开号：US20010011075A1

  公开（公告）日：2001-08-02

  The present invention relates to polysubstituted benzimidazoles, having the following formula: 1 wherein Q is a substituted benzimidazole group attached at the benzimidazole 1-position; R is a halogen of atomic number 9 to 53, inclusive (i.e., —F, —Cl, —Br, or —I); azido (i.e., —N 3 ); or —X—R 1 , wherein X is a chalcogen of atomic number 8 to 16, inclusive (i.e., —O— or —S—), and R 1 may be straight or branched chain alkyl of 1 to 8 carbon atoms; and R 2 and R 3 may be the same or different and are separately —O—C(═O)CH 3 (i.e., —OAc) or hydroxy (i.e., —OH); and pharmaceutically acceptable salts and operative combinations thereof. Also provided by this invention are compositions comprising a polysubstituted benzimidazole as defined above and methods of use thereof.

  本发明涉及具有下式的多取代苯并咪唑： 1 其中 Q 是连接在苯并咪唑 1 位上的取代苯并咪唑基团；R 是原子序数为 9 至 53（含）的卤素（即 -F、-Cl、-Br 或 -I）；叠氮（即 -N 3 ）；或 -X-R 1 其中 X 是原子序数为 8 至 16（包括 8 和 16）的缩醛（即 -O- 或 -S-），而 R 1 可以是 1 至 8 个碳原子的直链或支链烷基；以及 R 2 和 R 3 可以相同或不同，并分别为-O-C(═O)CH 3 (即-OAc)或羟基(即-OH)；以及药学上可接受的盐及其作用组合。本发明还提供了包含如上定义的多取代苯并咪唑的组合物及其使用方法。
• Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-.beta.-D-ribofuranosyl analogs of AMP, GMP, IMP, and CMP
  作者：Natarajan Raju、Donald F. Smee、Roland K. Robins、Morteza M. Vaghefi

  DOI：10.1021/jm00126a027

  日期：1989.6

  Methyl 2,3-O-isopropylidene-D-ribofuranoside (1) was converted to 1-O-acetyl-5-bromo-5-deoxy-2,3-di-O-benzoyl-D-ribofuranose (6) in five steps with good yield. The Arbuzov condensation of compound 6 with triethyl phosphite resulted in the synthesis of 1-O-acetyl-2,3-di-O-benzoyl-5-deoxy-5-(diethoxyphosphinyl)-D-ribofuranos e (7). Compound 7 was used for direct glycosylation of both purine and pyrimidine bases. The glycosylation was accomplished with the dry silylated heterocyclic base in the presence of trimethylsilyl triflate. Deblocking of the glycosylation products gave exclusively the beta anomer of the 5'-phosphonate analogues of 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]adenine (13), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]guanosin e (16), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]hypoxant hine (17), and 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]cytosine (15), described here for the first time. The target compounds as well as their intermediates showed no in vitro antiviral or antitumor activity, although phosphorylation of 15 and 16 to di- and triphosphate analogues was demonstrated with use of isolated cellular enzymes.