Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester | 640273-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6R)-5-azido-2-(phenylmethoxymethyl)-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]-3-(2,2,2-trifluoroethoxysulfonyloxy)oxan-4-yl] benzoate
• CAS: 640273-67-2
• 化学式: C₃₄H₄₀F₃N₃O₁₄S
• 分子量: 803.765
• InChiKey: LYFXFRBGZWRIQY-LJBNDJDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到2-azido-6-O-benzyl-2-deoxy-4-O-sulfonato-β-D-galactopyranosyl-(1-6)-1.2:3.4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131
• 作为产物：
  描述：

  Benzoic acid (3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-hydroxy-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester 在 4 A molecular sieve 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Sulfo-Protected Hexosamine Monosaccharides:  Potentially Versatile Building Blocks for Glycosaminoglycan Synthesis

  摘要：

  [GRAPHICS]2,2,2-Trifluorodiazoethane was investigated as a reagent for sulfo group protection on hexosamine monosaccharides. The synthesis of glucosamine and galactosamine building blocks fully differentiated for glycosaminoglycan synthesis and the synthesis of glycosyl donors are described. The compatibility of trifluoroethylsulfonate under a variety of reaction conditions has also been investigated.

  DOI：

  10.1021/ol035882w