Sulfuric acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 2,2,2-trifluoro-ethyl ester | 640273-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Sulfuric acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 2,2,2-trifluoro-ethyl ester
• CAS: 640273-50-3
• 化学式: C₂₃H₃₆F₃N₃O₈SSi
• 分子量: 599.701
• InChiKey: QQCTVETWOFQOTB-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  149.28
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyol-3-O-benzyl-4-O-chloroacetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 、 Sulfuric acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 2,2,2-trifluoro-ethyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以44%的产率得到tert-hexyldimethylsilyl (methyl-2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosylfuronate)-(1-3)-2-azido-3-O-benzyl-2-deoxy-6-O-trifluoroethylsulfonato-β-D-glucopyranoside
  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：

  Sulfuric acid mono-[(2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl] ester 在 三氟乙酸 、 柠檬酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Sulfuric acid (2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 2,2,2-trifluoro-ethyl 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