methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside | 133635-44-6

• 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: methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside
• 英文别名: [(2S)-5-methoxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 133635-44-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: WQBSHXUHUCJVCS-UEWDXFNNSA-N

物化性质

• 沸点：
  354.8±32.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside 在 palladium on activated charcoal 硫酸氢铵 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 氨 、 氢气 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙醇 为溶剂， 45.0~120.0 ℃ 、379.21 kPa 条件下， 反应 59.0h， 生成 [(2S,5R)-5-(7-aminoimidazo[4,5-b]pyridin-3-yl)tetrahydrofuran-2-yl]methanol
  参考文献：
  名称：

  1-deazaadenine核苷N6-环烷基衍生物的合成和生物学评估：一类新的抗人类免疫缺陷病毒药物。

  摘要：

  一系列带有N6氮的未取代或带有甲基或环烷基取代基的1-deazaadenine核苷，其2位上有或没有氯基，且糖基部分为核糖（1-16），2'-脱氧核糖（17从5,7-二氯-3H-咪唑并[4,5-b]吡啶（50）开始设计和合成-32）或2'，3'-二脱氧核糖（33-48）。评估了这些化合物的抗人免疫缺陷病毒1型（HIV-1）和单纯疱疹病毒1型（HSV-1）的体外活性。此外，还测试了它们抑制小牛肠腺苷脱氨酶（ADA）的能力。尽管母体化合物1-deazaadenosine（9），2'-deoxy-1-deazaadenosine（25）和2'，3'-dideoxy-1-deazaadenosine（41）和相应的2-chloro衍生物均无活性，与2'，3'-二脱氧腺苷相比，在N6上带有环烷基取代基的核苷具有中等至良好的抗HIV-1活性，其改善的程度和方式取决于糖部分的结构。通常，2'-脱氧-和2

  DOI：

  10.1021/jm00020a017
• 作为产物：
  描述：

  ((3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-yl)methyl 4-methylbenzoate 在 偶氮二异丁腈 、 5%-palladium/activated carbon 、 camphor-10-sulfonic acid 、 氢气 、 三正丁基氢锡 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside
  参考文献：
  名称：

  METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE

  摘要：

  提供了一种通过将通用式（I）表示的化合物与硫化合物反应的步骤来制备通式（II）表示的化合物的生产方法。在通式（I）和（II）中，R1代表氢原子或酰基，R2代表氢原子、氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基，R3代表氢原子或酰氧基，R5代表烷基或芳基，X代表离去基团。在R2为氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基的情况下，R3为酰氧基。

  公开号：

  US20160355536A1

文献信息

• Synthesis of 2′-Azido, 2,2′-Anhydro and 2′,5′-Anhydro Nucleosides with Potential Anti-HIV Activity
  作者：Ahmed E. -S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1055/s-1991-26454

  日期：——

  Reaction of methyl 2-bromo-2,3-dideoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (7) with silylated uracils 9 using trimethylsilyl triflate as catalyst afforded the corresponding 2′-bromonucleosides 10. 2,3-Didehydro sugar 8 was prepared by heating 7 with sodium azide in dimethylformamide. 2,2′-Anhydro nucleosides 1 were prepared by treating the nucleosides 10 with sodium methoxide at room temperature. 1-(2-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine (15) and its α-anomer (16) were prepared by treating 10c with sodium azide and subsequently methanolic ammonia. Treatment of 1-(2-bromo-2,3-dideoxy-α-D-erythro-pentofuranosyl)thymine (11 c) with excess of sodium methoxide under reflux gave the corresponding 2′,5'′anhydro nucleoside 17.

  以三甲基硅烷基三氟甲烷为催化剂，将 2-溴-2,3-二脱氧-5-O-(4-甲基苯甲酰基)-D-赤式戊呋喃糖苷（7）与硅化尿嘧啶 9 反应，得到相应的 2′-溴核苷 10。将 7 与叠氮化钠在二甲基甲酰胺中加热，制备出 2,3-二脱氢糖 8。室温下用甲醇钠处理核苷 10，制备 2,2′-脱氢核苷 1。1-(2-Azido-2,3-dideoxy-δ²-D-threo-pentofuranosyl)thymine (15) 及其 δ-anomer (16) 是用叠氮化钠和甲醇氨处理 10c 而制备的。在回流条件下，用过量甲醇钠处理 1-(2-溴-2,3-二脱氧-δ-D-赤式-戊呋喃糖基)胸腺嘧啶(11 c)，可得到相应的 2′,5'′脱氢核苷 17。
• METHOD FOR PRODUCTING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
  申请人：FUJIFILM Corporation

  公开号：EP3109245A1

  公开（公告）日：2016-12-28

  There is provided a production method of a compound represented by the following formula (II) through a step of reacting a compound represented by the following General Formula (I) with a sulfur compound. In General Formulas (I) and (II), R1 represents a hydrogen atom or an acyl group, R2 represents a hydrogen atom, a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R3 represents a hydrogen atom or an acyloxy group, R5 represents an alkyl group or an aryl group, and X represents a leaving group. Here, in a case where R2 is a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R3 is an acyloxy group.

  本发明提供了一种下式(II)化合物的生产方法，其步骤是将下式(I)化合物与硫化合物反应。 在通式（I）和（II）中，R1 代表氢原子或酰基，R2 代表氢原子、氟原子、酰氧基、芳基甲基氧基、烯丙基氧基、芳基甲基氧基羰基氧基或烯丙基氧基羰基氧基，R3 代表氢原子或酰氧基，R5 代表烷基或芳基，X 代表离去基团。 这里，在 R2 是氟原子、酰氧基、芳基甲基氧基、烯丙基氧基、芳基甲基氧基羰基氧基或烯丙基氧基羰基氧基的情况下，R3 是酰氧基。
• Inhibitory Effects of 1-Deazaadenosine Analogues on HIV Replication and Adenosine Deaminase
  作者：Sauro Vittori、Rosaria Volpini、Emidio Camaioni、Giorgio Palúg、Giorgio Cristalli

  DOI：10.1080/15257779508012435

  日期：1995.5.1

  A series of 2',3'-dideoxy-N-6-(cyclo)alkyl-1-deazaadenosine derivatives were synthesized starting from 2,6-dichloro-1-deazapurine (9). The new nucleosides proved to be good inhibitors of HIV-1 replication, the most active being the 2',3'-dideoxy-2-chloro-N-6-cycloctyl-1-deazaadenosine (14h, ED(50) = 0.4 mu M).
• Synthesis of 2?,3?-dideoxynucleosides from 5-alkoxymethyluracils
  作者：Ahmed E. -S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1007/bf00815166

  日期：——

  A modified synthesis of protected 2,3-dideoxyribose 5 starting from L-glutamic acid (1) is described. Reaction of 5 with silylated 5-hydroxymethyluracil 7 a and 5-alkoxymethyluracils 7 b-e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2',3'-dideoxyuridine derivatives 8 a-e and 9 a-e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides 10 a-e and 11 a-e. Treatment of 9 b-e with tri(1H-1,2,4-triazol-1-yl) phosphine oxide and subsequent reaction of 12 b-e with ammonia in dioxane afforded the cytosine derivatives 13 b-e which on treatment with methanolic ammonia gave the corresponding 2',3'-dideoxycytidine derivatives 14 b-e and 15 b-e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).
• Diazepinone Nucleosides as Inhibitors of Cytidine Deaminase.
  作者：G. Cristalli、R. Volpini、S. Vittori、E. Camaioni、G. Rafaiani、S. Potenza、A. Vita

  DOI：10.1080/07328319608002457

  日期：1996.10

  The synthesis of 2'-deoxy and 2',3'-dideoxy derivatives of 1-beta-D-ribofuranosyl-1,3,4,7-tetrahydro-2H-1,3- diazepin-(2)-one (2) was undertaken in order to find new cytidine deaminase (CDA) inhibitors and potential adjuvants in anticancer chemotherapy. Replacement of ribose by a 2-deoxyribose moiety led to compound 9 that appeared slightly more potent than 2 (Ki=2.5x10(-8) M). Remarkably, the corresponding alpha-2'-deoxynucleoside 10 acted as a very potent inhibitor of human placenta CDA, with a Ki=7.5x10(-8) M. Attempt to synthesize the 2',3'-dideoxy derivative of 2 led to N-[4,5-dihydroxy-1-(2-oxo-2,3,4,7-tetrahydro[1,3]diazepin-1-yl)-pentyl] -2,2,2-trifluoroacetamide (13), which is devoid of CDA inhibitory activity.