3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-galactopyranosyl bromide | 153252-80-3

• 分子结构分类: 有机化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-galactopyranosyl bromide
• 英文别名: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-bromo-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester；TrocNH(-2d)a-Gal1Br3Ac4Ac6Ac；[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 153252-80-3
• 化学式: C₁₅H₁₉BrCl₃NO₉
• 分子量: 543.58
• InChiKey: IGLJUTJCXNPQND-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-galactopyranosyl bromide 在 4 A molecular sieve 、 camphor-10-sulfonic acid 、 盐酸胍 、 sodium 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.33h， 生成 4-pentenyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)

  摘要：

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.041
• 作为产物：
  描述：

  2-deoxy-2[[(2,2,2-trichloroethoxy)carbonyl]amino]-D-galactopyranose 1,3,4,6-tetraacetate 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 以95%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)

  摘要：

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.041

文献信息

• Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline
  作者：Sergey S. Pertel、Elena S. Kakayan、Alexander I. Zinin、Leonid O. Kononov

  DOI：10.1016/j.carres.2024.109040

  日期：2024.2

  A synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline – a previously unknown 2-alkoxy glyco-[2,1-d]-2-oxazoline derivative with d-galacto configuration was carried out. Glycosylating activity of the obtained galactooxazoline has been studied and it has been shown that in the presence of a weak protic acid, such as sym-collidinium triflate, this

  2-(2,2,2-三氯乙氧基)-(3,4,6-三-O-乙酰基-1,2-二脱氧基-α- d-吡喃半乳糖)-[2,1- d ]-2的合成-恶唑啉–一种以前未知的具有d-半乳糖构型的 2-烷氧基糖-[2,1- d ]-2-恶唑啉衍生物。对所得半乳恶唑啉的糖基化活性进行了研究，结果表明，在弱质子酸（例如sym -collidinium triflate）存在下，该物质表现出反应性和 1,2-反式立体选择性糖基供体的特性。已发现糖的恶唑啉衍生物的均聚反应在相同条件下进行，导致假低聚糖产物的形成。人们发现，这种不希望的副反应可以通过改变酸催化剂浓度来抑制，从而开发出使用合成的2-(2,2, 2-三氯乙氧基)-2-恶唑啉糖基供体在非常温和的条件下。
• The synthesis of oligosaccharides containing internal and terminal Galβ1-3GlcNAcβ fragments
  作者：V. V. Severov、G. V. Pazynina、T. V. Ovchinnikova、N. V. Bovin

  DOI：10.1134/s1068162015020120

  日期：2015.3

  Oligosaccharides Gal beta 1-3GlcNAc beta-sp, GlcNAc beta 1-3Gal beta 1-3GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-3Gal beta 1-3GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-6Gal beta 1-4GlcNAc beta-sp (sp = O(CH2)(3)NH2 or O(CH2)(2)NH2) were synthesized using glycosylation with N-Troc-protected derivatives of glucosamine or disaccharide Le(c).