3-O-benzoyl-1,2-O-isopropylidene-α-D-galactofuranose | 53942-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzoyl-1,2-O-isopropylidene-α-D-galactofuranose
• 英文别名: 3-O-Benzoyl-1,2-O-isopropyliden-α-D-galaktofuranose；3-O-Benzoyl-1,2-O-isopropyliden-α-D-galactofuranose；[(3aR,5S,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 53942-36-2
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: FVMGHHSPTSHJCW-NLRWUALESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzoyl-1,2-O-isopropylidene-α-D-galactofuranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-3,6-di-O-benzoyl-β-D-galactofuranose
  参考文献：
  名称：

  First synthesis of the immunodominant β-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus

  摘要：

  beta-Galf-(1 --> 5)-p-Galf-(1 --> 6)-alpha-Manp-(1 --> 6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra- O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)-2-O-acetyl- 3,6-di-O-benzoyl-beta-D -galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.019
• 作为产物：
  描述：

  1,2:5,6-Di-O-isopropyliden-3-O-benzoyl-α-D-galaktofuranose 在 sodium hydrogen sulfate 、 silica gel 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 3.0h， 以99%的产率得到3-O-benzoyl-1,2-O-isopropylidene-α-D-galactofuranose
  参考文献：
  名称：

  使用二氧化硅负载的硫酸氢钠作为多相催化剂对丙酮化物进行简单易行的化学和区域选择性脱保护

  摘要：

  已发现二氧化硅负载的硫酸氢钠 (NaHSO4·SiO2) 是一种有效的多相催化剂，可用于在室温下对丙酮化物进行化学和区域选择性脱保护，以优异的产率生产相应的二醇。

  DOI：

  10.1246/cl.2003.734

文献信息

• Reckendorf, Wolfgang Meyer zu; Schultz, Norbert; Kreimeier, Richard, Liebigs Annalen der Chemie, 1994, # 4, p. 337 - 346
  作者：Reckendorf, Wolfgang Meyer zu、Schultz, Norbert、Kreimeier, Richard

  DOI：——

  日期：——
• A Simple and Facile Chemo- and Regioselective Deprotection of Acetonides Using Silica Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst
  作者：G. Mahender、R. Ramu、C. Ramesh、Biswanath Das

  DOI：10.1246/cl.2003.734

  日期：2003.8

  Silica supported sodium hydrogen sulfate (NaHSO4·SiO2) has been found to be an efficient heterogeneous catalyst for chemo- and regioselective deprotection of acetonides at room temperature to produce the corresponding diols in excellent yields.

  已发现二氧化硅负载的硫酸氢钠 (NaHSO4·SiO2) 是一种有效的多相催化剂，可用于在室温下对丙酮化物进行化学和区域选择性脱保护，以优异的产率生产相应的二醇。
• First synthesis of the immunodominant β-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus
  作者：Mingkun Fu、Guohua Zhang、Jun Ning

  DOI：10.1016/j.carres.2004.10.019

  日期：2005.1

  beta-Galf-(1 --> 5)-p-Galf-(1 --> 6)-alpha-Manp-(1 --> 6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra- O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)-2-O-acetyl- 3,6-di-O-benzoyl-beta-D -galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection. (C) 2004 Elsevier Ltd. All rights reserved.