3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose" | 88238-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose"
• 英文别名: 3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-tagato-sucrose
• CAS: 88238-32-8
• 化学式: C₂₂H₃₂O₁₂
• 分子量: 488.489
• InChiKey: HKBSLZVLRKOVHY-OYJGKJDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  129.74
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  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 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 54.17h， 生成 3,4-anhydro-1,6-di-O-trityl-β-D-lyxo-hexulofuranosyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  3,6'-di-O-acetyl-4,6:2,1'-di-O-isopropylidene-tagato-sucrose 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose"
  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

• Derivatives of sucrose 3′,4′-epoxide
  作者：R.D. Guthrie、Ian D. Jenkins、San Thang、Ryohei Yamasaki

  DOI：10.1016/0008-6215(83)84010-5

  日期：1983.9

  Abstract A facile, one-pot synthesis of α- d -glucopyranosyl 3,4-anhydro-β- d -tagatofuranoside (1) from sucrose in good yield is reported. Derivatives of 1 can also be obtained from 4,6:2,1′-di-O-isopropylidenesucrose and from 2,3,6,1′,6′-penta-O-benzoylsucrose by treatment with triphenylphosphine and diethyl azodicarboxylate. The n.m.r. spectra (13C,1H) and conformation of derivatives of 1 are discussed

  摘要报道了一种由蔗糖容易地一锅合成高产α-d-吡喃葡萄糖基3,4-脱水-β-d-塔呋喃呋喃糖苷（1）的方法。通过用三苯基膦和偶氮二羧酸二乙酯处理，还可以从4,6：2,1'-二-O-异亚丙基蔗糖和2,3,6,1'，6'-戊-O-苯甲酰蔗糖获得衍生物1。讨论了nmr光谱（13C，1H）和1的衍生物的构象。报道了一种新的无水蔗糖（1'，4'）。