2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate | 130783-15-2

• 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-5-thio-α-D-xylopyranosyl trichloroacetimidate
• 英文别名: 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl；2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl trichloroacetimidate；2,3,4-tri-O-acetyl-5-thio-α-xylopyranosyl trichloroacetimidate；2,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate；[(3S,4S,5R,6S)-4,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxythian-3-yl] acetate
• CAS: 130783-15-2
• 化学式: C₁₃H₁₆Cl₃NO₇S
• 分子量: 436.698
• InChiKey: AIYZSOOLMTXXQW-YTWAJWBKSA-N

物化性质

• 沸点：
  419.4±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate 在 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-[2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)-1-hydroxyethyl]benzonitrile
  参考文献：
  名称：

  New 1-C-(5-thio-d-xylopyranosyl) derivatives as potential orally active venous antithrombotics

  摘要：

  In the search for new orally active antithrombotic drugs that are metabolically stable, we explored the synthesis of 1-C-(5-thio-D-xylosyl) derivatives, examining radical and nucleophilic methods. Thus synthesized were aryl, benzyl, alkylcarboxymethylenyl, arylsulfonylmethylenyl and alkylaminocarboxymethylenyl C-linked analogues of 5-thio-D-xylopyranosides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00147-2
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-5-thio-α-D-xylopyranose 在 乙酸肼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate
  参考文献：
  名称：

  1,2,3,4-四-O-乙酰基-5-硫代-d-吡喃吡喃糖的经济合成及其转化为具有抗血栓形成活性的4-取代的苯基1,5-二硫代-d-吡喃吡喃糖苷11第五部分。第四部分，见[1] .22，部分提交于第九届欧洲碳水化合物研讨会，乌得勒支，1997年7月6日至11日，摘要。A16。

  摘要：

  D-木糖经1,2-O-异亚丙基-α-D-木呋喃糖（4）转化为3-O-苯甲酰基-5-S-苯甲酰基-1,2-O-异亚丙基-α-D-木呋喃糖，甲醇分解后，乙酰化和随后的乙酰分解得到1,2,3,4-四-O-乙酰基-5-硫代-α-D-吡喃木糖（14），总产率为36％。4与亚硫酰氯的反应得到非对映体环状亚硫酸盐的混合物，其结构通过X射线晶体学确定。用高碘酸钠氧化得到相应的环状硫酸盐23。用硫代乙酸钾处理23，得到5-S-乙酰基1,2-O-异亚丙基-α-D-木呋喃糖3-O-磺酸的钾盐（26 ），在甲醇分解，乙酰化和随后的乙酰分解后，得到14，总产率为56％。用硫酰氯处理4得到含有5-氯-3-O-氯磺酰基-5-脱氧-1,2-O-异亚丙基-α-D-木呋喃糖，3,7,9,11-四氧杂-4-的混合物硫代-10-二甲基-三环[6,3,0,0（2,6）]十一烷S-二氧化物和23的比例为2：3：7。将四乙酸酯14转化

  DOI：

  10.1016/s0008-6215(98)00088-3

文献信息

• A Kinetic Isotope Effect Study on the Hydrolysis Reactions of Methyl Xylopyranosides and Methyl 5-Thioxylopyranosides:  Oxygen versus Sulfur Stabilization of Carbenium Ions
  作者：Deepani Indurugalla、Andrew J. Bennet

  DOI：10.1021/ja011232g

  日期：2001.11.1

  (J. Am. Chem. Soc. 1986, 108, 7287-7294) KIEs for the acid-catalyzed hydrolysis of methyl alpha- and beta-glucopyranosides, it is possible to conclude that at the transition state for xylopyranoside hydrolysis resonance stabilization of the developing carbenium ion by the ring oxygen atom is coupled to exocyclic C-O bond cleavage, and the corresponding methyl glucopyranosides hydrolyze via transition

  以下动力学同位素效应 KIEs (k(light)/k(heavy))，分别在 HClO(4) (mu = 1.0 M, NaClO( 4)) 在 80 摄氏度：alpha-D，1.128 +/- 0.004，1.098 +/- 0.005；β-D, 1.088 +/- 0.008, 1.042 +/- 0.004; 伽马-D(2)、(C5) 0.986 +/- 0.001、0.967 +/- 0.003；离去基团 (18)O, 1.023 +/- 0.002, 1.023 +/- 0.003; 环 (18)O, 0.983 +/- 0.001, 0.978 +/- 0.001; 异头 (13)C, 1.006 +/- 0.001, 1.006 +/- 0.003; 和溶剂，0.434 +/- 0.017、0.446 +/- 0.012。结合报道的 (J. Am. Chem. Soc. 1986
• Novel thioxylose compounds, preparation method thereof, pharmaceutical compositions containing same and use thereof in therepeutics.
  申请人：Barberousse Veronique

  公开号：US20070054955A1

  公开（公告）日：2007-03-08

  The invention relates to novel 5-thioxylose compounds, preferably derivatives of the 5-thioxylopyranose type, to the method for their preparation and to their use as active principles of drugs intended especially for the treatment or prevention of thromboses or cardiac insufficiency.

  这项发明涉及新型的5-硫氧木糖化合物，优选为5-硫氧木糖吡喃糖类衍生物，以及它们的制备方法，以及它们作为药物活性成分的用途，特别用于治疗或预防血栓或心脏功能不全。
• Novel Compounds Derived From 5-Thioxylose And Their Use In Therapeutics
  申请人：Barberousse Veronique

  公开号：US20080293768A1

  公开（公告）日：2008-11-27

  The invention relates to novel 5-thioxylose compounds, preferably derivatives of the 5-thioxylopyranose type, to the process for their preparation and to their use as active principles of drugs intended especially for the treatment or prevention of thrombosis or cardiac insufficiency.

  这项发明涉及新颖的5-硫木糖化合物，优选为5-硫木糖吡喃糖类衍生物，以及它们的制备过程和它们作为药物活性成分的用途，主要用于治疗或预防血栓形成或心脏功能不全。
• Derivatives of 5-Thioxylopyranose and Use of Same for Treatment
  申请人：Barberousse Veronique

  公开号：US20090182013A1

  公开（公告）日：2009-07-16

  The invention relates to new compounds of 5-thioxilose, preferably derivatives of the 5-thioxilopyranose type, and to a method for preparing the same and their use as the active ingredient of drugs mainly intended for treating or inhibiting thrombosis or heart failure or thromboembolic diseases.

  该发明涉及5-硫代木糖的新化合物，优选为5-硫代木糖吡喃糖类的衍生物，以及一种制备这些化合物的方法和它们作为药物活性成分的用途，主要用于治疗或抑制血栓形成、心力衰竭或血栓栓塞性疾病。
• .beta.-D-phenylthioxylosides, their method of preparation and their use
  申请人：Fournier Industrie et Sante

  公开号：US05101048A1

  公开（公告）日：1992-03-31

  The present invention relates, by way of novel industrial products, to the .beta.-D-phenylthioxyloside compounds of the formula ##STR1## in which: X represents a sulfur atom or an oxygen atom; R.sub.1, R.sub.2 and R.sub.3, which are identical or different, each represent a hydrogen atom, a nitro group, a cyano group, a group --CO--R (in which R represents a C.sub.1 -C.sub.4 alkyl group or a trifluoromethyl group), an amino group, an acetamido group (NHCOCH.sub.3), a C.sub.1 -C.sub.4 alkoxy group, a trifluoromethyl group or a phenyl group substituted by one or more cyano, nitro or trifluoromethyl groups, it being possible for R.sub.1 and R.sub.2, taken together, to form, with the phenyl group to which they are bonded, a .beta.-naphthalenyl group which is unsubstituted or substituted by one or more cyano, nitro or trifluoromethyl groups; and Y represents the hydrogen atom or an aliphatic acyl group. These compounds are useful as therapeutic agents, especially as venous antithrombotics.

  本发明涉及一种新型工业产品，即β-D-苯硫氧木糖苷化合物，其化学式为##STR1##其中：X代表硫原子或氧原子；R.sub.1、R.sub.2和R.sub.3，它们相同或不同，分别代表氢原子、硝基、氰基、--CO--R基团（其中R代表C.sub.1-C.sub.4烷基或三氟甲基基团）、氨基、乙酰胺基团（NHCOCH.sub.3）、C.sub.1-C.sub.4烷氧基团、三氟甲基基团或一个或多个氰基、硝基或三氟甲基基团取代的苯基，其中R.sub.1和R.sub.2可以一起与它们连接的苯基形成一个未取代或一个或多个氰基、硝基或三氟甲基基团取代的β-萘基；Y代表氢原子或脂肪族酰基。这些化合物可用作治疗剂，特别是作为静脉抗血栓药物。