4'-chloro-4'-deoxysucrose | 111829-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-chloro-4'-deoxysucrose
• 英文别名: Fruf4Cl(b2-1a)Glc；(2R,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-4-chloro-3-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 111829-08-4
• 化学式: C₁₂H₂₁ClO₁₀
• 分子量: 360.746
• InChiKey: MBSKDBJEHKBNSO-UGDNZRGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose" 在 sodium methylate 、 溶剂黄146 、 lithium chloride 作用下， 以 甲醇 为溶剂， 反应 26.17h， 生成 4'-chloro-4'-deoxysucrose
  参考文献：
  名称：

  Ring-opening reactions of sucrose epoxides: Synthesis of 4′-derivatives of sucrose

  摘要：

  The 2,1''-O-isopropylidene derivative (1) of 3-O-acetyl-4,6-O-isopropylidene-.alpha.-D-glucopyranosyl 6-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside and 2,3,4-tri-O-acetyl-6-O-trityl-.alpha.-D-glucopyranosyl 3,4-anhydro-1,6-di-O-trityl-.beta.-D-lyxo-hexulofuranoside have been synthesised and 1 has been converted into 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside (2). The SN2 reactions of 2 with azide and chloride nucleophiles gave the corresponding 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-azido-4-deoxy-.beta.-D-fructofuranoside (6) and 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-chloro-4-deoxy-.beta.-D-fructofuranoside (8), respectively. The azide 6 was catalytically hydrogenated and the resulting amine was isolated as 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 4-acetamido-1,3,6-tri-O-acetyl-4-deoxy-.beta.-D-fructofuranoside. Treatment of 5 with hydrogen bromide in glacial acetic acid followed by conventional acetylation gave 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-bromo-4-deoxy-.beta.-D-fructofuranoside. Similar SN2 reactions with 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-ribo-hexulofuranoside (12) resulted in a number of 4''-derivatives of .alpha.-D-glucopyranosyl .beta.-D-sorbofuranoside. The regiospecific nucleophilic substitution at position 4'' in 2 and 12 has been explained on the basis of steric and polar factors.

  DOI：

  10.1016/0008-6215(87)80215-x

文献信息

• Sweet chlorine-substituted disaccharides
  申请人：TATE & LYLE PUBLIC LIMITED COMPANY

  公开号：EP0050952A1

  公开（公告）日：1982-05-05

  Newcompoundsofthegeneralformula (in which the 3'- and 4'- substituents have a trans configuration with respect to each other) are potent sweeteners and can be formuiated as compositions. They can be made by direct chlorination of a sucrose derivative blocked at the 6- position; by chlorination of 4-chloro-4-deoxy- β-D-fructofuranosyl α-D-glucopyranoside blocked at the 6- position; or by introducing the 4'- chloro substituent by treatment with diethylazodicarboxylate and triphenylphosphine followed by contact with a source of chloride ions, the other chloro substituents being introduced into the molecule before or afterthis reaction.

  一般式样的新化合物（其中 3'- 和 4'- 取代基相互之间具有反式构型）是一种强效甜味剂，并可制成组合物。 它们可以通过以下方法制成：直接氯化 6- 位受阻的蔗糖衍生物；氯化 6- 位受阻的 4-氯-4-脱氧-β-D-呋喃果糖基 α-D-吡喃葡萄糖苷；或通过用偶氮二甲酸二乙酯和三苯基膦处理引入 4'- 氯取代基，然后与氯离子源接触，在此反应之前或之后将其他氯取代基引入分子中。
• US4405654A
  申请人：——

  公开号：US4405654A

  公开（公告）日：1983-09-20
• Ring-opening reactions of sucrose epoxides: Synthesis of 4′-derivatives of sucrose
  作者：Riaz Khan、Michael R. Jenner、Harold Lindseth、Khizar S. Mufti、Gita Patel

  DOI：10.1016/0008-6215(87)80215-x

  日期：1987.5

  The 2,1''-O-isopropylidene derivative (1) of 3-O-acetyl-4,6-O-isopropylidene-.alpha.-D-glucopyranosyl 6-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside and 2,3,4-tri-O-acetyl-6-O-trityl-.alpha.-D-glucopyranosyl 3,4-anhydro-1,6-di-O-trityl-.beta.-D-lyxo-hexulofuranoside have been synthesised and 1 has been converted into 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside (2). The SN2 reactions of 2 with azide and chloride nucleophiles gave the corresponding 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-azido-4-deoxy-.beta.-D-fructofuranoside (6) and 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-chloro-4-deoxy-.beta.-D-fructofuranoside (8), respectively. The azide 6 was catalytically hydrogenated and the resulting amine was isolated as 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 4-acetamido-1,3,6-tri-O-acetyl-4-deoxy-.beta.-D-fructofuranoside. Treatment of 5 with hydrogen bromide in glacial acetic acid followed by conventional acetylation gave 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-bromo-4-deoxy-.beta.-D-fructofuranoside. Similar SN2 reactions with 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-ribo-hexulofuranoside (12) resulted in a number of 4''-derivatives of .alpha.-D-glucopyranosyl .beta.-D-sorbofuranoside. The regiospecific nucleophilic substitution at position 4'' in 2 and 12 has been explained on the basis of steric and polar factors.