3-(trifluoroacetamido)propyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 121042-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(trifluoroacetamido)propyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 3-trifluoroacetamidopropyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(phenylmethoxymethyl)-6-[3-[(2,2,2-trifluoroacetyl)amino]propoxy]oxan-4-yl] acetate
• CAS: 121042-74-8
• 化学式: C₂₂H₂₉F₃N₂O₈
• 分子量: 506.476
• InChiKey: WXIYTCAPQOTBRT-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-(trifluoroacetamido)propyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 N-{3-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-4-benzyloxymethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-propyl}-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  Synthesis of histo blood-group antigens A and B (type 2), xenoantigen Galα1-3Galβ1-4GlcNAc and related type 2 backbone oligosaccharides as haptens in spacered form

  摘要：

  The partial alpha-fucosylation of spacered (sp = CH2CH2CH2NH2) N-acetyl beta-lactosamine derivative having free hydroxy groups at C-3 and C-2' gives rise to oligosaccharides H (type 2), Le(x) and Le(y), the first one was further elongated giving rise to A (type 2) or B (type 2) tetrasaccharides; spacered trisaccharides Galalpha1-3Galbeta1-4GlcNAc and Galalpha1-4Galbeta1-4GlcNAc were synthesised by the partial alpha-galactosylation of N-acetyl beta-lactosamine derivative, having free hydroxy groups at C-4' and C-3'.

  DOI：

  10.1070/mc2002v012n04abeh001591
• 作为产物：
  描述：

  β-Ac3GlcNAc-sp3 在 吡啶 、 甲醇 、 三乙基硅烷 、 sodium methylate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 27.0h， 生成 3-(trifluoroacetamido)propyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] LARGE SCALE PRODUCTION OF N-ACETYLLACTOSAMINE DERIVATIVES
  [FR] PRODUCTION À GRANDE ÉCHELLE DE DÉRIVÉS DE N-ACÉTYLLACTOSAMINE

  摘要：

  Methods of preparing N-acetyllactosamine derivatives for use in the preparation 3'-O-glycosyl- and 2',3'-di-O-glycosyl-N-acetyllactosamine derivatives are described. The methods avoid the use of column chromatography and allow for the preparation of multigram quantities of the synthons.

  公开号：

  WO2023194941A1

文献信息

• Block synthesis of A (type 2) and B (type 2) tetrasaccharides related to the human ABO blood group system
  作者：Ivan M. Ryzhov、Elena Yu. Korchagina、Inna S. Popova、Tatiana V. Tyrtysh、Alexander S. Paramonov、Nicolai V. Bovin

  DOI：10.1016/j.carres.2016.04.029

  日期：2016.7

  Herein we report the synthesis of 3-aminopropyl glycosides of A (type 2) and B (type 2) tetrasaccharides via [3 + 1] block scheme. Peracetylated trichloroacetimidates of A and B trisaccharides were used as glycosyl donors. The well-known low reactivity of 4-OH group of N-acetyl-d-glucosamine forced us to test four glucosamine derivatives (3-Bz-1,6-anhydro-GlcNAc and 3-trifluoroacetamidopropyl β-glycosides

  在本文中，我们通过[3 +1]嵌段方案报告了A（2型）和B（2型）四糖的3-氨基丙基糖苷的合成。A和B三糖的全乙酰化三氯乙酰亚氨酸酯用作糖基供体。N-乙酰基-d-葡糖胺的4-OH基团众所周知的低反应性迫使我们测试四种葡糖胺衍生物（3-Ac-的3-Bz-1,6-anhydro-GlcNAc和3-三氟乙酰氨基丙基β-糖苷6-Bn-GlcNAc，3-Ac-6-Bn-GlcNc3和3-Ac-6-Bn-GlcNAc2）来选择用于合成2型四糖的最佳糖基受体。当3-Ac-6-Bn-GlcNAcβ的3-三氟乙酰氨基丙基糖苷被糖基化时，没有分离出所需的四肽。3-Bz-1，6-脱水-GlcNAc衍生物的糖基化产生α-糖苷作为主要产物。只有将3-三氟乙酰氨基丙基3-Ac-6-Bn-GlcNAc2β用作糖基受体（β/α5：1），而与A的三氯乙酰亚氨酸酯进行糖基化反应时，只有在B（2型）四糖的合成中才能实现高立体特异性。三糖不是立体定向的（β/α1
• The synthesis of linear trilactosamine
  作者：G. V. Pazynina、V. V. Severov、N. V. Bovin

  DOI：10.1134/s1068162008050129

  日期：2008.9

  TrilactosamineGal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, where sp = O(CH(2))(3)NH(2) is a spacer, was synthesized. The tetrasaccharide fragment Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp was obtained by successive glycosylation using elongation by one monosaccharide residue at a time; and the tetrasaccharide was then transformed into a hexasaccharide with a disaccharide glycosyl donor. A 2,2,2-trichloroethoxycarbonyl group was used for the protection of the glucosamine amino group.
• Synthesis of monosulfated saccharides in the spacered form
  作者：Tatyana V. Ovchinnikova、Ekaterina V. Shipova、Marina A. Sablina、Galina V. Pazynina、Inna S. Popova、Aleksandr B. Tuzikov、Nicolai V. Bovin

  DOI：10.1070/mc2002v012n06abeh001652

  日期：2002.1

  The sulfated (Su) saccharides 3-Su-Galbeta, 3-Su-GaINAcbeta, 4-Su-GalNAcbeta, 6-Su-GalNAcalpha, 6-Su-GlcNAcbeta, 6-Su-LacNAcbeta, 6'-Su-LacNAcbeta, 3'-Su-Galbeta1-3GlcNAcbeta and 3'-Su-Galbeta1-3GalNAcalpha, all monosaccharides in D-configuration, have been synthesised in the form of 3-aminopropyl or 3-trifluoroacetamidopropyl glycosides.
• Use of methanesulfonic acid in the reductive ring-opening of O-benzylidene acetals
  作者：Alexander I. Zinin、Nelly N. Malysheva、Anna M. Shpirt、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2006.10.009

  日期：2007.2

  Methanesulfonic acid was shown to be an efficient and convenient substitute for ethereal HCl in reductive 4,6-O-benzylidene acetal ring-opening reaction with sodium cyanoborohydride in THF. Normal regioselectivity was observed, the 6-O-benzyl ethers with free 4-OH group being the major products of the reaction. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of glycoprotein N-chain core fragment GlcNAcβ1-4(Fucα1-6)GlcNAc
  作者：Galina V. Pazynina、Svetlana V. Tsygankova、Nicolai V. Bovin

  DOI：10.1016/j.mencom.2015.07.004

  日期：2015.7

  Synthesis of Ac(3)GlcNAc beta(1-4)-3-Ac-6-BnGlcNTroc beta-O(CH2)(3)NHCOCF3, a convenient precursor for the preparation of 6-substituted derivatives of disaccharide GlcNAc beta 1-4GlcNAc, is described. alpha-Fucosylation of this precursor after the removal of protection groups leads to the title trisaccharide, whereas O-sulfation results in 6-O-sulfated derivative of chitobiose.