3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose | 160882-25-7

• 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: 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose
• 英文别名: 3-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol；1,4-anhydro-3-O-benzyl-4-thio-D-arabinitol；3-O-benzyl-1-deoxy-4-thio-D-arabinofuranose；(3S,4S,5R)-5-(hydroxymethyl)-4-phenylmethoxythiolan-3-ol
• CAS: 160882-25-7
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: ZLYPDNVLXMMXFI-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 9-[(3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine
  参考文献：
  名称：

  A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

  摘要：

  4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 mu g/mL, respectively).

  DOI：

  10.1021/jm9701536
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 吡啶 、 盐酸 、 甲醇 、 sodium sulfide 、 sodium tetrahydroborate 、 sodium periodate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose
  参考文献：
  名称：

  五层龙属植物中提取的锍鎓盐类天然产物neoponkoranol克级别的全合成方法

  摘要：

  本发明属于化学合成领域，具体涉及五层龙属植物中提取的具有降糖活性的锍鎓盐类天然产物neoponkoranol克级别的全合成方法。该方法由商业途径购买的D‑葡萄糖经多步反应以克级别合成五层龙属植物中提取的锍鎓盐类天然产物neoponkoranol。

  公开号：

  CN109305956A

文献信息

• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• A Novel Synthesis of 2‘-Modified 2‘-Deoxy-4‘-thiocytidines from <scp>d</scp>-Glucose¹
  作者：Yuichi Yoshimura、Kenji Kitano、Kohei Yamada、Hiroshi Satoh、Mikari Watanabe、Shinji Miura、Shinji Sakata、Takuma Sasaki、Akira Matsuda

  DOI：10.1021/jo9700540

  日期：1997.5.1

  antimetabolites, specifically several 2'-modified 2'-deoxy-4'-thiocytidines, were synthesized as potential new antineoplastic agents. Methyl 3-O-benzylxylofuranoside was converted to a 1,4-anhydro-4-thioarabitol 24. Protection of the primary alcohol of 24 gave a common intermediate (15) which was useful for the synthesis of various 2'-modified 2'-deoxy-4'-thionucleosides. Oxidation of the secondary hydroxyl

  合成了新型的2'-脱氧胞苷抗代谢物，特别是几种2'-修饰的2'-脱氧-4'-硫胞苷，作为潜在的新型抗肿瘤药。将3-O-苄基木呋喃糖苷甲基转化为1,4-脱水-4-硫代阿拉伯糖醇24。保护伯醇24得到通用中间体（15），该中间体可用于合成各种2'-修饰的2'-脱氧4'-硫代核苷。氧化15个仲羟基，然后进行Wittig反应或用（二乙基氨基）三氟化硫（DAST）处理，生成2-脱氧-2-亚甲基（26）和2-脱氧-2,2-二氟（34）衍生物， 分别。相应的亚砜和三甲基甲硅烷基化的N（4）-乙酰胞嘧啶之间的唯一Pummerer型糖基化反应产生2'-deoxy-2'-亚甲基-（10）和2'-deoxy-2'，2' -二氟-4'-硫胞苷（11）。另一方面，用DAST处理15引入了一个氟原子，保留了2'-立体化学，得到40。相反，使用5步从15获得的3-O-苯甲酰基衍生物53的Mitsunobu反应二苯基磷酰
• Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
  作者：Genzoh Tanabe、Kazuya Yoshikai、Takanori Hatanaka、Mizuho Yamamoto、Ying Shao、Toshie Minematsu、Osamu Muraoka、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2006.10.014

  日期：2007.6.1

  De-O-sulfonated analogs (10a, Y(-)=CH(3)OSO(3) and 10b, Y(-)=Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y(-)=CH(3)OSO(3)) with L-thiosugar moiety (1,4-dideoxy-1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol

  天然存在的糖苷酶抑制剂salacinol的De-O-磺化类似物（10a，Y（-）= CH（3）OSO（3）和10b，Y（-）= Cl）及其非对映异构体（12a，Y（-制备具有L-硫糖基部分（1,4-二脱氧-1,4-表硫基-L-阿拉伯糖醇）的）= CH（3）OSO（3））。检查了它们对肠道麦芽糖酶和蔗糖酶的抑制活性，并与亲本α-糖苷酶抑制剂salacinol（1a）进行了比较。化合物10a和10b对两种酶均显示出与1a相同的有效抑制活性，尽管12a是对蔗糖酶和麦芽糖酶的弱抑制剂。这些结果表明1a的O-磺酸根阴离子部分对于抑制活性不是必需的。
• A New Class of Glycosidase Inhibitor:  Synthesis of Salacinol and Its Stereoisomers
  作者：Ahmad Ghavami、Blair D. Johnston、B. Mario Pinto

  DOI：10.1021/jo001444g

  日期：2001.4.1

  Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitol

  Salacinol（4）是Salacia reticulata水提取物中的活性成分之一，传统上在斯里兰卡和印度用于治疗糖尿病。描述了水杨醇（4），水杨醇的对映体（5）和非对映体（7）的合成。合成策略依赖于2,3,5-三-O-苄基-1,4-脱水-4-硫代-D-或L-阿拉伯糖醇在C-1的2,4-O-亚苄基上的选择性亲核攻击D-或L-赤藓糖醇-1,3-环硫酸盐。这项工作旨在解决关于柳氮醇的确切结构的歧义，并最终确定天然产物的结构。
• Synthesis of iminothiasugar as a potential transition-state analog inhibitor of glycosyltransfer reactions
  作者：Hideya Yuasa、Tetsuya Kajimoto、Chi-Huey Wong

  DOI：10.1016/0040-4039(94)88293-2

  日期：1994.10

  Iminothiasugar 1, a potential transition-state analog inhibitor of glycosidases, was synthesized in 10 steps from D-xylose.

  从D-木糖分十步合成了糖胺糖苷的潜在过渡态类似物抑制剂Iminothiasugar 1。