2,3,4,3',4'-戊-O-乙酰基蔗糖 | 34382-02-0

• 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
• 中文名称: 2,3,4,3',4'-戊-O-乙酰基蔗糖
• 英文名称: 2,3,4,3',4'-penta-O-acetylsucrose
• 英文别名: (O³,O⁴-diacetyl-β-D-fructofuranosyl)-(O²,O³,O⁴-triacetyl-α-D-glucopyranoside)；(O³,O⁴-Diacetyl-β-D-fructofuranosyl)-(O²,O³,O⁴-triacetyl-α-D-glucopyranosid)；O²,O³,O⁴,O^3'_,O4'-Pentaacetyl-saccharose；2,3,3',4,4'-penta-O-acetylsucrose；sucrose pentaacetate；2,3,3',4,4'-Penta-O-acetyl-saccharose；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 34382-02-0
• 化学式: C₂₂H₃₂O₁₆
• 分子量: 552.486
• InChiKey: UMOFHQSJMUINFR-ZQNATQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  220
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,3,4,3',4'-戊-O-乙酰基蔗糖 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 276.0h， 生成 2,3,4,3',4'-penta-O-acetyl-6,6'-di-O-benzoyl-1'-O-trimsylsucrose
  参考文献：
  名称：

  Guthrie, R. D. (Gus); Jenkins, Ian D.; Watters, James J., Australian Journal of Chemistry, 1980, vol. 33, # 11, p. 2487 - 2497

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,3,4,3',4'-戊-O-乙酰基蔗糖
  参考文献：
  名称：

  Bredereck et al., Chemische Berichte, 1958, vol. 91, p. 2832,2841

  摘要：

  DOI：

文献信息

• Novel Chlorination Reagent and a Novel Process for Chlorination of Sugars Using Thionyl Chloride
  申请人：Ratnam Rakesh

  公开号：US20100228020A1

  公开（公告）日：2010-09-09

  Preparation of chlorinating reagent or chlorination reaction itself for use in a reaction such as production of high intensity sweetener trichlorogalactosucrose (TGS) from partially protected sucrose, comprising reaction of dimethylformamide (DMF) with thionyl chloride or another sulphur containing inorganic acid chlorides including sulphuryl chloride is faced with a problem of prolific release of gaseous by-products, that at times may lead to violent explosion also. This problem is solved by innovative addition of solid powder inert to the constituents of the chlorination reaction mixture to the reaction, or by adding DMF to acid chloride solution in that order. The invention also leads to use of isolated solid Vilsmeier reagent being used for chlorination in a solvent other than DMF making it possible to avoid altogether problems arising from use of DMF which include irrecoverable loss in alkaline as well as acid conditions, interference in crystallization of TGS and the like.

  用于反应中的氯化试剂的制备或氯化反应本身，例如从部分保护的蔗糖中生产高强度甜味剂三氯半乳糖（TGS），包括二甲基甲酰胺（DMF）与氯化亚砜或其他含硫无机酸氯化物（包括亚硫酰氯）反应，面临着大量释放气态副产物的问题，有时甚至可能导致剧烈爆炸。这一问题通过创新地向氯化反应混合物的成分中添加固体粉末惰性物质，或按顺序向酸氯化物溶液中添加DMF来解决。该发明还导致孤立固体维尔斯迈尔试剂用于在非DMF溶剂中进行氯化，从而避免完全使用DMF所带来的问题，包括在碱性和酸性条件下不可恢复的损失，对TGS结晶的干扰等。
• Process to Prepare Sucralose
  申请人：Rajadhyaksha Mangesh

  公开号：US20100184969A1

  公开（公告）日：2010-07-22

  The present invention relates to a process to prepare sucralose. More particularly the said process relates to the production of sucralose, chemically known as, 6-Dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-alpha-D-galactopyranoside of formula (1)

  本发明涉及一种制备三氯蔗糖的方法。更具体地说，该方法涉及生产三氯蔗糖，化学上称为6-二氯-1,6-二去氧-β-D-果糖呋喃甙-4-氯-4-去氧-α-D-半乳糖苷，化学式为(1)。
• Novel chlorination process for preparing sucralose
  申请人：Xu Shaojun

  公开号：US20080300392A1

  公开（公告）日：2008-12-04

  A process for preparing a sucralose-6-ester, a key intermediate to sucralose. The process contains (a) creating a heterogeneous mixture comprising a first phase comprising a sucrose-6-ester and a second phase comprising a chlorinating reagent; and (b) reacting the sucrose-6-ester with the chlorinating reagent, to prepare a sucralose-6-ester. In addition, processes for preparing sucralose from sucrose-6-esters are provided.

  一种制备三氯蔗糖-6-酯的方法，该酯是制备三氯蔗糖的关键中间体。该方法包括(a)制备一种异相混合物，其中第一相包括蔗糖-6-酯，第二相包括氯化试剂；(b)将蔗糖-6-酯与氯化试剂反应，制备三氯蔗糖-6-酯。此外，还提供了从蔗糖-6-酯制备三氯蔗糖的方法。
• Process for production of chlorinated sucrose based on hydrophobic affinity chromatography
  申请人：Ratnam Rakesh

  公开号：US20100222570A1

  公开（公告）日：2010-09-02

  This invention relates to a process for selective capture, isolation and purification of chlorinated sucrose compounds, including chlorinated sucrose, their precursors and derivatives, including trichlorogalactosucrose (TGS), directly from chlorinated reaction mixture by column chromatography on adsorbents and under conditions which result in specific and selective affinity towards one or more of chlorinated sucrose compound. The process also integrates de-esterification of chlorinated sucrose esters adsorbed on the adsorbent while they are being treated with desorbent. The process also provides a novel approach to concentration and crystallization of TGS. The chlorinated sucrose derivatives, including TGS, thus isolated are substantially free from most impurities, salts and organic solvents. The process has high recovery of more than 95% in terms of desired chlorinated sucrose derivatives including TGS.

  本发明涉及一种从氯化反应混合物中通过吸附剂柱层析和在特定条件下对氯化蔗糖化合物，包括氯化蔗糖、其前体和衍生物，如三氯半乳糖蔗糖（TGS）进行选择性捕获、分离和纯化的过程。该过程还结合了在吸附剂上吸附的氯化蔗糖酯在处理解吸剂时的去酯化。该过程还提供了一种新的浓缩和结晶TGS的方法。因此，分离出的包括TGS在内的氯化蔗糖衍生物基本上不含大多数杂质、盐和有机溶剂。该过程具有高达95%以上的期望氯化蔗糖衍生物，包括TGS的高回收率。
• Branched-chain sucroses: Synthesis and Wittig reaction of the 1′-aldehydo derivative of sucrose
  作者：Riaz Khan、Gita Patel

  DOI：10.1016/0008-6215(87)80216-1

  日期：1987.5

  the 6,1′,6′-tris( tert -butyldiphenylsilyl) derivative 2 (27%) and the 6,6′-bis( tert -butyldiphenylsilyl) derivative (67%). Oxidation of the HO-1′ in 3 with methyl sulphoxide and trifluoroacetic anhydride gave the 1′-aldehydo derivative 5 , which reacted with the stabilised Wittig reagent (Ph 3 PCHCO 2 Et) to give the 1′-ethoxycarbonylmethylene derivative 6 . Deacetylation of the hepta-acetate 7 of

  摘要2,3,4,3'，4'-戊基-O-乙酰蔗糖（1）与3.3 mol的反应。当量 叔丁基二苯基甲硅烷基氯在吡啶中，在4-二甲基氨基吡啶存在下，得到6,1'，6'-三（叔丁基二苯基甲硅烷基）衍生物2（27％）和6,6'-双（叔丁基二苯基甲硅烷基） ）衍生工具（67％）。用甲基亚砜和三氟乙酸酐氧化3中的HO-1'，得到1'-醛衍生物5，其与稳定的Wittig试剂（Ph 3PCHCO2 Et）反应，得到1'-乙氧基羰基亚甲基衍生物6。用甲醇甲醇钠使6的乙酸七酯7脱乙酰化，同时进行迈克尔加成反应，得到2,1'-脱水-1'-甲氧基羰基甲基蔗糖。