2,3,4,6-Tetra-O-benzoyl-α-D-glucopyranosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-Tetra-O-benzoyl-α-D-glucopyranosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2:3,4-di-Oisopropylidene-α-D-galactopyranose；[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl benzoate
• 化学式: C₄₆H₄₆O₁₅
• 分子量: 838.862
• InChiKey: NQPXFVHSHQKQMV-XRARPGJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 [t-Bu₂SnOH(Cl)]2 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 2,3,4,6-Tetra-O-benzoyl-α-D-glucopyranosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2

  摘要：

  Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu(2)SnOH(Cl)](2). The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.

  DOI：

  10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-h

文献信息

• OFox imidates as versatile glycosyl donors for chemical glycosylation
  作者：Swati S. Nigudkar、Tinghua Wang、Salvatore G. Pistorio、Jagodige P. Yasomanee、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1039/c6ob02230h

  日期：——

  mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical

  以前，我们交流了3,3-二氟己二酮（HOFox）介导的糖基化作用，其中发现3,3-二氟-3 H-吲哚-2-基（OFox）酰亚胺化是关键中间体。无论是在原位由相应的糖基溴化物和亚胺酸酯OFox活化合成可以在再生的方式进行。在这里，我们扩展了这项研究，主要侧重于各种OFox酰亚胺的合成及其作为化学1,2-顺式和1,2-反式糖基化的糖基供体的研究。
• Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2
  作者：Akihiro Orita、Yuuki Hamada、Takehiko Nakano、Shinji Toyoshima、Junzo Otera

  DOI：10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-h

  日期：2001.8.3

  Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu(2)SnOH(Cl)](2). The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.