(2S,3R,4S)-4,6-bis(acetyloxy)-2-methyloxan-3-yl acetate | 71155-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-4,6-bis(acetyloxy)-2-methyloxan-3-yl acetate
• 英文别名: [(2S,3R,4S)-3,6-diacetyloxy-2-methyloxan-4-yl] acetate
• CAS: 71155-56-1
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: QKPIXQGRPBEVLX-QBSMBOLCSA-N

物化性质

• 熔点：
  111-112 °C(Solv: isopropanol (67-63-0))
• 沸点：
  333.1±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-4,6-bis(acetyloxy)-2-methyloxan-3-yl acetate 在 吡啶 、 acide p-toluenesulfonique 、 silver fluoride 作用下， 以 苯 为溶剂， 反应 170.5h， 生成 (2S,3R,4S,6S)-6-(((3S,4S,6S)-4-azido-6-(benzyloxy)-2-methylenetetrahydro-2H-pyran-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  寡糖合成方法。Hemisynthese de la 4'- o-（2-desoxy l-fucosyl）柔红霉素

  摘要：

  二糖4- O-（3,4-二-O-乙酰基-2,6-双脱氧-α-1-lyxo-己吡喃糖基）-2，3,6-三脱氧-3-三氟乙酰氨基-l- lyxo的制备描述了-六吡喃糖11c，其N，N'-二甲基衍生物天然存在于许多蒽环类中。用柔红霉素进行糖基化，然后除去保护基，产生4′- O-（2-脱氧-1-岩藻糖基）柔红霉素。

  DOI：

  10.1016/0040-4020(81)85015-6
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 吡啶 、 N-甲基咪唑 、 氢溴酸 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.25h， 生成 (2S,3R,4S)-4,6-bis(acetyloxy)-2-methyloxan-3-yl acetate
  参考文献：
  名称：

  [EN] DRUG CONJUGATES OF SUGAR DERIVATIVES AND USES THEREOF AS SENOLYTIC AGENTS
  [FR] CONJUGUÉS MÉDICAMENTEUX DE DÉRIVÉS DE SUCRE ET LEURS UTILISATIONS EN TANT QU'AGENTS SÉNOLYTIQUES

  摘要：

  Provided herein are agents and methods for selectively killing senescent cells that are associated with numerous pathologies and diseases, including age-related pathologies and diseases. As disclosed herein, senescent cell-associated diseases and disorders may be treated or prevented by administering at least one senolytic agent or pharmaceutical compositions thereof. The senescent cell-associated diseases or disorders treated or prevented by the agents and methods described herein include, but are not limited to, cardiovascular diseases or disorders, cardiovascular diseases and disorders associated with arteriosclerosis, such as atherosclerosis, idiopathic pulmonary fibrosis (IPF), chronic obstructive pulmonary disease (COPD), osteoarthritis, inflammatory or autoimmune diseases or disorders, pulmonary diseases or disorders, neurological diseases or disorders, dermatological diseases or disorders, chemotherapeutic side effects, radiotherapy side effects, metastasis and metabolic diseases.

  公开号：

  WO2023039600A1

文献信息

• 14-Fluoroanthracyclines. Novel syntheses and antitumor activity.
  作者：TERUYO MATSUMOTO、MASAKO OHSAKI、KAORU YAMADA、FUYUHIKO MATSUDA、SHIRO TERASHIMA

  DOI：10.1248/cpb.36.3793

  日期：——

  The 14-fluoroanthracyclines (5-10) carrying L-daunosamine, D-2-deoxyribose, or L-2-deoxyfucose as their glycosidic sugar moieties, were synthesized starting from (-)-7-deoxy-4-demethoxydaunomycinone ((R)-11a) or (-)-7-deoxydaunomycinone ((R)-11b). As key steps, the synthetic route features a novel fluorination reaction in which tetrabutylammonium fluoride is employed in the presence of a half equivalent of p-toluenesulfonic acid, and the previously explored glycosidation reaction in which trimethylsilyl trifluoromethanesulfonate is utilized as an activating reagent. In P388 in vivo tests, 5, 6, 9, and 10 exhibited prominent cytotoxicity comparable with that of adriamycin (1). Notable antitumor activity was also observed for 6 and 9 in P388 in vivo tests.

  以(-)-7-脱氧-4-去甲氧基大芸霉素酮((R)-11a)或(-)-7-脱氧大芸霉素酮((R)-11b)为出发点，合成了以L-脱氨基糖、D-2-脱氧核糖或L-2-脱氧岩藻糖为糖苷键的14-氟蒽环类化合物(5-10)。作为关键步骤，该合成路线采用了新颖的氟化反应，即在对甲苯磺酸的半当量存在下使用四丁基氟化铵，以及之前探索过的糖苷化反应，即使用三甲基硅基三氟甲磺酸盐作为活化试剂。在 P388 体内试验中，5、6、9 和 10 表现出与阿霉素（1）相当的显著细胞毒性。在 P388 体内试验中，还观察到 6 和 9 具有显著的抗肿瘤活性。
• Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using <i>S</i>-But-3-ynyl Thioglycoside Donors
  作者：Surya Adhikari、Kedar N. Baryal、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1021/cs300670k

  日期：2013.1.4

  A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy alpha-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2-deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford alpha-selective glycosides in good to excellent yields.
• Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures
  作者：Heidrun Schene

  DOI：10.1055/s-1999-3651

  日期：1999.8
• MATSUMOTO, TERUYO;OHSAKI, MASAKO;YAMADA, KAORU;MATSUDA, FUYUHIKO;TERASHIM+, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3793-3804
  作者：MATSUMOTO, TERUYO、OHSAKI, MASAKO、YAMADA, KAORU、MATSUDA, FUYUHIKO、TERASHIM+

  DOI：——

  日期：——
• [EN] NOVEL SUGAR DERIVATIVES AND USES THEREOF TO PREPARE NOVEL SENOLYTIC AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS DE SUCRE ET LEURS UTILISATIONS POUR PRÉPARER DE NOUVEAUX AGENTS SÉNOLYTIQUES
  申请人：[en]RUBEDO LIFE SCIENCES, INC.

  公开号：WO2023039292A2

  公开（公告）日：2023-03-16

  Provided herein are novel sugar derivatives which are intermediates for preparing senolytic agents that selectively kill senescent cells associated with numerous pathologies and diseases, including age-related pathologies and diseases.