2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl chloride | 15067-04-6

• 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: 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl chloride
• 英文别名: (2R,3R,4S,5R,6R)-2-((Benzoyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3,4,5-triyl tribenzoate；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-chlorooxan-2-yl]methyl benzoate
• CAS: 15067-04-6
• 化学式: C₃₄H₂₇ClO₉
• 分子量: 615.036
• InChiKey: RPAFUVNYMMOOKJ-RLXMVLCYSA-N

物化性质

• 熔点：
  116-118 °C
• 沸点：
  726.7±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl chloride 、 甲醇 生成 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Indium(III) Triflate–Mediated One-Step Preparation of Glycosyl Halides from Free Sugars

  摘要：

  In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glycosides in the same pot by reacting them with the respective alcohols in good yield.

  DOI：

  10.1080/00397910903419886
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 氯氧化铋 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  Highly stereoselective synthesis of peracylated α-aldopyranosyl chlorides from aldopyranose peracetates and thionyl chloride catalyzed by BiCl3 generated in situ from the procatalyst BiOCl

  摘要：

  Aldopyranose peracetates react with thionyl chloride and BiCl3, generated in situ from a substoichiometric amount of the procatalyst BiOCl, producing the corresponding peracylated aldopyranosyl chlorides in very good to excellent yields (82-97%) with exclusive alpha-anomeric selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.138

文献信息

• METHOD FOR PRODUCING a-HALO-TETRAACYL-GLUCOSE
  申请人：MITSUBISHI TANABE PHARMA CORPORATION

  公开号：US20160002276A1

  公开（公告）日：2016-01-07

  There is provided an efficient and excellent preparation method of an α-halo-tetraacyl-glucose which is suitable for industrial preparation, which comprises reacting D-glucose or lower alkyl D-glucoside with a reactive derivative of a carboxylic acid and a metal halide to prepare the α-halo-tetraacyl-glucose represented by the formula (III): wherein R represents an optionally substituted lower alkyl group or an optionally substituted aryl group, and X represents a halogen atom, in one step, and the resulting α-halo-tetraacyl-glucose (III) can be converted into a compound of the formula (I) or a salt thereof by subjecting to a conventional method.

  提供了一种适用于工业制备的高效、优秀的α-卤代四酰基葡萄糖的制备方法，该方法包括将D-葡萄糖或低级烷基D-葡萄糖苷与羧酸的活性衍生物和金属卤化物反应，以制备由公式(III)表示的α-卤代四酰基葡萄糖：其中R代表一个可选地被取代的低级烷基团或一个可选地被取代的芳基团，X代表一个卤素原子，一步完成，并且得到的α-卤代四酰基葡萄糖(III)可以通过常规方法转化为公式(I)的化合物或其盐。
• Efficient Synthesis of α-Glycosyl Chlorides Using 2-Chloro-1,3-dimethylimidazolinium Chloride: A Convenient Protocol for Quick One-Pot Glycosylation
  作者：Madhu Babu Tatina、Duc Thinh Khong、Zaher M. A. Judeh

  DOI：10.1002/ejoc.201800360

  日期：2018.5.24

  A convenient method for the synthesis of α‐glycosyl chloride donors in high 80–96 % yields within 15–30 min using 2‐chloro‐1,3‐dimethylimidazolinium chloride has been developed. The method enables quick and direct one‐pot glycosylation reactions in high overall yields.

  已经开发了一种方便的方法，可以使用2-氯-1,3-二甲基咪唑啉鎓盐在15-30分钟内以80-96％的高产率合成α-糖基氯供体。该方法可实现快速，直接的一锅糖基化反应，且总收率高。
• 一种在温和条件下制备卤代糖的方法
  申请人：陕西师范大学

  公开号：CN111269279B

  公开（公告）日：2022-08-05

  本发明公开了一种在温和条件下制备卤代糖的方法，利用易于制备的硫苷供体与卤素单质或卤素互化物在室温下反应，即可得到卤代糖(氯、溴、碘)。其中所述的卤素单质和卤素互化物分别是商业易得碘单质、溴化碘以及氯化碘。该方法适用于各类吡喃糖和呋喃糖。且该方法对于硫苷供体的保护基没有限制，可以是吸电子基团如乙酰基、苯甲酰基等，也可以是供电子的基团如苄基、硅基等。同时该反应在二氯甲烷、乙腈、甲苯等多种有机溶剂中均可发生。本发明卤代糖的制备方法简单，反应条件温和，原料易得，适用范围广，对于酸不稳定的基团如异亚丙基缩酮和硅基等具有兼容性，而且对于分离过程不稳定的卤代糖除去溶剂即可得到纯净的产物。
• Synthesis of glycosyl chlorides using catalytic Appel conditions
  作者：Imlirenla Pongener、Kirill Nikitin、Eoghan M. McGarrigle

  DOI：10.1039/c9ob01544b

  日期：——

  stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly

  描述了使用催化Appel条件立体选择性合成糖基氯。使用一定范围的糖基半缩醛，草酰氯和5 mol％的Ph3PO，可获得高产率的α-糖基氯。对于2-脱氧糖，在没有氧化膦催化剂的情况下用草酰氯处理相应的半缩醛也得到了良好的糖基氯收率。该方法操作简单，并且可以容易地除去5mol％的氧化膦副产物。或者，可以进行一锅多催化剂糖基化以将糖基半缩醛直接转化为糖苷。
• Mild method for the synthesis of α-glycosyl chlorides: A convenient protocol for quick one-pot glycosylation
  作者：Ariza Khanam、Shashiprabha Dubey、Pintu Kumar Mandal

  DOI：10.1016/j.carres.2023.108976

  日期：2023.12

  A simple and efficient protocol for the preparation of α-glycosyl chlorides within 15–30 min is described which employs a stable, cheap, and commercially available Trichloroisocyanuric acid (TCCA) as non-toxic chlorinating agent along with PPh3. This process involved a wide range of substrate scope and is well-suited with labile hydroxyl protecting groups such as benzyl, acetyl, benzoyl, isopropylidene

  描述了一种在 15-30 分钟内制备 α-糖基氯的简单而有效的方案，该方案采用稳定、廉价且市售的三氯异氰尿酸 (TCCA) 作为无毒氯化剂以及 PPh 3 。该过程涉及广泛的底物范围，并且非常适合不稳定的羟基保护基团，例如苄基、乙酰基、苯甲酰基、异丙叉基、亚苄基和TBDPS（叔丁基二苯基甲硅烷基）基团。该工艺操作简单，条件温和，收率良好，α选择性优良。此外，可以进行多催化剂一锅糖基化，以高总产率将糖基半缩醛直接转化为各种O-糖苷，而不需要分离或纯化α-糖基氯供体。