α-D-glucopyranosyl 3,4-anhydro-β-D-tagatofuranoside | 76520-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl 3,4-anhydro-β-D-tagatofuranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(1S,2S,4R,5S)-2,4-bis(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 76520-78-0；84142-57-4
• 化学式: C₁₂H₂₀O₁₀
• 分子量: 324.285
• InChiKey: OHYOKHJZKDWWSD-OGDLUYPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.35
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  161.6
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl 3,4-anhydro-β-D-tagatofuranoside 在 氢溴酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 54.03h， 生成 4'-bromo-4'-deoxysucrose hepta-acetate
  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-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose" 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 α-D-glucopyranosyl 3,4-anhydro-β-D-tagatofuranoside
  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'）。
• 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：——
• GUTHRIE, R. D.;JENKINS, IAN D.;THANG, SAN;YAMASAKI, RYOHEI, CARBOHYDR. RES., 176,(1988) N 2, 306-308
  作者：GUTHRIE, R. D.、JENKINS, IAN D.、THANG, SAN、YAMASAKI, RYOHEI

  DOI：——

  日期：——