3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 58399-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: 3-deoxy-3-C-ethoxycarbonylmethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-3-deoxy-3-(2-ethoxy-2-oxoethyl)-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-3-C-ethoxycarbonylmethyl-alpha-D-allofuranose；ethyl 2-[(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate
• CAS: 58399-55-6
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: JTLSAHIMVJUEAS-IGJDLRFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 高氯酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate
  参考文献：
  名称：

  WO2008/23336

  摘要：

  公开号：
• 作为产物：
  描述：

  [(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-acetic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以78%的产率得到3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  通过闭环复分解来差异连接β-C-二糖的统一方法。

  摘要：

  DOI：

  10.1021/ja010641+

文献信息

• Highly stereoselective total synthesis of tylonolide, the aglycon of the 16-membered macrolide antibiotic tylosin. I. Construction of the C-1-C-8 chiral centers.
  作者：TATSUYOSHI TANAKA、YUJI OIKAWA、TATSUO HAMADA、OSAMU YONEMITSU

  DOI：10.1248/cpb.35.2209

  日期：——

  In order to synthesize tylonolide, the aglycon of the 16-membered macrolide antibiotic tylosin, a Prelog-Djerassi lactone-type compound (4) corresponding to the C-1-C-9 segment was synthesized from D-glucose. Benzyl-type protecting groups for hydroxy functions, such as benzyl, 4-methoxybenzyl, and 3, 4-dimethoxybenzyl groups, as well as some cyclic and acyclic stereocontrolled reactions, such as hydroboration, catalytic hydrogenation, and Grignard reaction, were successfully employed.

  为了合成 16 元大环内酯抗生素泰洛新的苷元--泰洛内酯，以 D-葡萄糖为原料合成了与 C-1-C-9 段相对应的 Prelog-Djerassi 内酯型化合物 (4)。该化合物成功地采用了苄基、4-甲氧基苄基和 3，4-二甲氧基苄基等苄基型羟基保护基团，以及一些环状和非环状立体控制反应，如氢硼化反应、催化氢化反应和格氏反应。
• Total synthesis of tylonolide, the aglycone of the 16-membered ring macrolide tylosin, from D-glucose. Selective application of MPM and DMPM protecting groups for hydroxy functions
  作者：Tatsuyoshi Tanaka、Yuji Oikawa、Tatsuo Hamada、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(00)84872-8

  日期：1986.1

  Segments i (C11–C17) and ii (C1–C10), synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protecting groups, were esterified and cyclized to the 16-membered enone, which was readily converted to tylonolide, the aglycone of tylosin.

  通过D-葡萄糖通过一些立体选择性反应和苄基型保护基合成的片段i（C11–C17）和ii（C1–C10）被酯化并环化为16元烯酮，该烯酮很容易转化为噻咯烷内酯，泰乐菌素的糖苷配基。
• Influence of ring fusion stereochemistry on the stereochemical outcome in photo-induced Diels–Alder reaction of fused bicycloheptenone derivatives
  作者：Subrata Ghosh、Sritama Bose、Anupam Jana、A. Nijamudheen、Ayan Datta

  DOI：10.1016/j.tet.2014.11.025

  日期：2014.12

  Photo-isomerization of cis-cycloheptenone fused to a ring with a defined stereochemistry at the ring fusion to its trans-stereoisomer and in situ Diels–Alder reaction with cyclic and acyclic dienes have been investigated. The reaction was found to proceed through one of the two possible isomerized trans-enones that produce the thermodynamically more stable adduct with a trans-fused seven-membered ring

  研究了顺式-环庚烯酮与环的光异构化，该环与环上的反式立体异构体融合时具有确定的立体化学，并研究了与环状和无环二烯的原位Diels-Alder反应。发现该反应通过两种可能的异构化反式链烯之一进行，所述反式链烯与反式稠合的七元环系统产生了热力学上更稳定的加合物。该方案已被用来构建具有反式融合的6-7环系统的四环，其核心结构存在于几个萜烯中。观察到的选择性已通过计算方法得到支持。
• MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Sattigeri Viswajanani J.

  公开号：US20100081610A1

  公开（公告）日：2010-04-01

  The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over-activation of a matrix metalloproteinase using the compounds.

  本发明涉及β-羟基和氨基取代的羧酸，其作为基质金属蛋白酶抑制剂，尤其是对映异构体纯的β-羟基羧酸，以及合成该类化合物和含有本发明化合物的制药组合物的相关过程。本发明化合物在治疗各种炎症、自身免疫和过敏性疾病方面有用，例如治疗哮喘、类风湿性关节炎、慢性阻塞性肺疾病、鼻炎、骨关节炎、银屑病性关节炎、牛皮癣、肺纤维化、创伤愈合障碍、肺炎炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、新内膜增生导致再狭窄和缺血性心力衰竭、中风、肾脏疾病、肿瘤转移以及其他以基质金属蛋白酶过度表达和过度活化为特征的炎症性疾病的方法中使用该化合物。
• Matrix metalloproteinase inhibitors
  申请人：Ranbaxy Laboratories Limited

  公开号：EP2322507A1

  公开（公告）日：2011-05-18

  The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over-activation of a matrix metalloproteinase using the compounds.

  本发明涉及作为基质金属蛋白酶抑制剂的β-羟基和氨基取代的羧酸，特别是非对映异构纯的β-羟基羧酸，以及合成本发明化合物的相应工艺和含有本发明化合物的药物组合物。本发明的化合物可用于治疗各种炎症、自身免疫性和过敏性疾病，如治疗哮喘、类风湿性关节炎、慢性阻塞性肺病、鼻炎、骨关节炎、银屑病关节炎、牛皮癣、肺纤维化、伤口愈合障碍、肺部炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、多发性骨髓瘤、多发性硬化症、多发性硬化症的方法、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、导致再狭窄和缺血性心力衰竭的新内膜增生、中风、肾脏疾病、肿瘤转移，以及其他以基质金属蛋白酶过度表达和过度激活为特征的炎症性疾病。