2,3,4,6,-tetra-O-acetyl-α-D-glucopyranosyl-1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside | 67909-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6,-tetra-O-acetyl-α-D-glucopyranosyl-1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6,-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside；2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside；2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside；2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-β-D-tagatofuranoside
• CAS: 67909-41-5；67909-42-6；104012-35-3
• 化学式: C₂₄H₃₂O₁₆
• 分子量: 576.508
• InChiKey: QQHGQPVCVPFMNR-XYWBLFRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  198.02
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6,-tetra-O-acetyl-α-D-glucopyranosyl-1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside 在 aluminum oxide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以30.5%的产率得到2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 6-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside
  参考文献：
  名称：

  Capek, Karel; Vydra, Tomas; Ranny, Mojmir, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 10, p. 2191 - 2200

  摘要：

  DOI：
• 作为产物：
  描述：

  蔗糖八乙酸酯 在 potassium carbonate on alumina 、 sodium methylate 、 乙酸酐 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 18.02h， 生成 2,3,4,6,-tetra-O-acetyl-α-D-glucopyranosyl-1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside
  参考文献：
  名称：

  Capek, Karel; Vodrazkova-Medonosova, Monika; Moravcova, Jitka, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 7, p. 1476 - 1486

  摘要：

  DOI：

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'）。
• Capek, Karel; Vydra, Tomas; Sedmera, Petr, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 6, p. 1317 - 1332
  作者：Capek, Karel、Vydra, Tomas、Sedmera, Petr

  DOI：——

  日期：——
• Oxirane-oxetane-1,4-dioxane anhydro-ring migration in sucrose derivatives
  作者：Karel Čapek、Tomáš Vydra、Petr Sedmera

  DOI：10.1016/0008-6215(87)80021-6

  日期：1987.10
• Guthrie, R. D.; Jenkins, Ian D.; Yamasaki, Ryohei, Carbohydrate Research, 1980, vol. 85, p. C5 - C6
  作者：Guthrie, R. D.、Jenkins, Ian D.、Yamasaki, Ryohei

  DOI：——

  日期：——
• 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.