2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranose | 151895-53-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranose
• 英文别名: 2,3,4-tri-O-acetyl-1-thio-L-fucopyranose；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-2-methyl-6-sulfanyloxan-3-yl] acetate
• CAS: 151895-53-3
• 化学式: C₁₂H₁₈O₇S
• 分子量: 306.337
• InChiKey: BWMDVFOFYSJKHO-MOBXTKCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 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：
  89.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranose 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-aminomethylsulfanyl-6-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Thio-sugars IV: Design and synthesis of S-linked fucoside analogs as a new class of α-L-fucosidase inhibitors

  摘要：

  alpha-1-Thio-L-fucose derivative 4 and 5 as new alpha-fucosidase inhibitors (K-1 = 4.6, and 5.9 mu M) have been synthesized in three steps by base catalyzed coupling with bromonitromethane followed by reduction of the nitro group with sodium borohydride/cobalt chloride complex and acetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00596-4
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose 在 DL-dithiothreitol 、 amino acetaldehyde acetal 作用下， 以89%的产率得到2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranose
  参考文献：
  名称：

  1→6,1→4和1→3连接的1-硫代-α-L-呋喃核糖基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和1→2连接的β-D-吡喃半乳糖苷的合成及其连接对α-L-岩藻糖苷酶的特异性抑制活性

  摘要：

  通过磺酸盐的取代反应和开环反应，合成了三种α-L-呋喃二糖基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和一种α-L-呋喃二糖基β-D-吡喃半乳糖苷的硫连接二糖类似物。 1-硫代-α-L-呋喃琼脂糖衍生物作为亲核试剂测定氮丙啶和环氧乙烷衍生物。所有这些二糖类似物均抑制了来自牛肾和附睾的岩藻糖苷酶，其Ki值范围为0.65至4.9 mM。

  DOI：

  10.1016/s0040-4039(00)74055-x

文献信息

• Stereoselective Epimerizations of Glycosyl Thiols
  作者：Lisa M. Doyle、Shane O’Sullivan、Claudia Di Salvo、Michelle McKinney、Patrick McArdle、Paul V. Murphy

  DOI：10.1021/acs.orglett.7b02760

  日期：2017.11.3

  Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains

  糖基硫醇广泛用于立体选择性S-糖苷合成中。使用TiCl 4获得了它们从1,2-反式到1,2-顺式硫醇的差向异构化（例如，在硫代吡喃葡萄糖中赤道到轴向差向异构），而SnCl 4促进了它们的轴向-赤道差向异构。该方法包括用于立体选择性β- d-甘露聚糖和β- 1- rhamnopyranosyl硫醇形成的应用。当使用SnCl 4时，络合物的形成解释了赤道偏爱，而TiCl 4可以通过1,3-氧杂硫杂环戊烷的形成使平衡向1，2-顺式硫醇转移。
• Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations
  作者：Begoña Aguilera、Alfonso Fernández-Mayoralas、Carlos Jaramillo

  DOI：10.1016/s0040-4020(97)00246-9

  日期：1997.4

  A cyclic 2,3-sulfamidate derived from has been treated with a variety of S-, N-, O-, and C-nucleophiles, leading to nucleophilic displacement at C-3, elimination, or deacetylation reactions depending on the type of nucleophile used. Nucleophilic displacement is achieved with thio-nucleophiles and NaN3, allowing the preparation of 3-thio- or 3-azido glucosamine derivatives difficult to obtain by use

  衍生自环状的2，3-氨基磺酸盐已用多种S-，N-，O-和C-亲核试剂处理，根据亲核试剂的类型，导致C-3处的亲核置换，消除或脱乙酰反应用过的。用硫亲核试剂和NaN 3可以实现亲核取代，从而可以制备难以通过使用磺酸盐获得的3-硫代或3-叠氮基葡糖胺衍生物。
• FUCOSE DERIVATIVES, DRUGS CONTAINING THE SAME AS ACTIVE INGREDIENT, AND INTERMEDIATES FOR PRODUCING THE SAME
  申请人：KANEBO, LTD.

  公开号：EP0859005A1

  公开（公告）日：1998-08-19

  A compound of the formula (I): wherein X1 is a group of one of the following formulae (1), (2) and (3): R1 is a branched long chain alkyl group, R2 is ―CONHR3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.

  式 (I) 的化合物： 其中 X1 是下式（1）、（2）和（3）之一的基团： R1是支链长链烷基，R2是-CONHR3、羧基或氢原子，n是0、1或2的整数，R3是低级烷基或苯基，或其药学上可接受的盐，可作为选择素抑制剂，用于预防或治疗各种炎症性疾病，如炎症性皮炎（如、特应性皮炎、接触性过敏、光敏性皮肤病等）、自身免疫性慢性疾病（如类风湿性关节炎、慢性甲状腺炎等）以及缺血再灌注损伤。
• Electrochemical nickel-catalyzed cross-coupling of glycosyl thiols with preactivated phenols and ketones
  作者：Fuxin Li、Hui Liu、Wanyu Xing、Qingju Zhang、Liming Wang

  DOI：10.1039/d4ob00442f

  日期：——

  An efficient electrochemical nickel-catalyzed cross-coupling reaction has been reported here for the synthesis of S-glycosides from preactivated phenols and ketones under mild conditions. Various glycosyl thiols, including unprotected sugar, and a diverse range of aryl/alkenyl triflates, including some complex biorelevant phenols and ketones, were well tolerated in this method.

  本文报道了一种有效的电化学镍催化交叉偶联反应，用于在温和条件下从预活化的酚和酮合成S-糖苷。该方法对各种糖基硫醇（包括未保护的糖）和各种芳基/烯基三氟甲磺酸酯（包括一些复杂的生物相关酚和酮）具有良好的耐受性。
• Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: application to the synthesis of thiooligosaccharides
  作者：Begoña Aguilera、Alfonso Fernández-Mayoralas

  DOI：10.1039/cc9960000127

  日期：——

  The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1'-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.