ethyl O-β-D-galactopyranosyl-(1-4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside | 186665-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl O-β-D-galactopyranosyl-(1-4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
• 英文别名: Gal(b1-4)[TrocNH(-2d)]Glc(b)-SEt；2,2,2-trichloroethyl N-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]carbamate
• CAS: 186665-12-3
• 化学式: C₁₇H₂₈Cl₃NO₁₁S
• 分子量: 560.834
• InChiKey: CQFIZFYADONOJM-ZSCXKYTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl O-β-D-galactopyranosyl-(1-4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 、 4-硝基苯基-α-D-吡喃半乳糖苷 在 α-D-galactosidase 、 sodium phosphate 作用下， 以 水 为溶剂， 反应 60.0h， 以120 mg的产率得到Galα1-3Galβ1-4GlcNTeocβ-SEt
  参考文献：
  名称：

  Glycosidase-catalysed synthesis of di- and trisaccharide derivatives related to antigens involved in the hyperacure rejection of xenotransplants

  摘要：

  A convenient enzymatic procedure, suitable for large scale preparation of the beta-thioethyl 2-N-Teoc-derivative of Ga1 alpha 1-3Gal beta 1-4GlcNAc, GalS1-4GlcNAc, is described (Teoc = 2,2,2-trichloroethoxycarbonyl). beta-D-Galactosidase from Bullera singularis was used for the specific synthesis of Gal beta 1-4GlcNTeoc beta-SEt from lactose and D-GlcNTeoc beta-SEt. alpha-D-Galactosidase from coffee beans was used for the stereo- specific and highly regioselective preparation of Gal alpha 1-3Gal beta 1-4GlcNTeoc beta-SEt, employing D-Gal alpha-OPhNO(2)-p as glycosyl donor and Gal beta 1-4GlcNTeoc beta-SEt as acceptor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02235-6
• 作为产物：
  描述：

  Lactose 、 ethyl 2-deoxy-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-glucopyranoside 在 sodium acetate buffer 、 yeast cells 作用下， 以 水 为溶剂， 反应 72.0h， 以19%的产率得到ethyl O-β-D-galactopyranosyl-(1-4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  糖苷酶修饰的碳水化合物的合成：乳糖胺衍生物和相关化合物的立体和区域特异性合成1

  摘要：

  摘要以不同的D-葡萄糖胺衍生物为接受剂，直接从乳糖以高克数级制备了在2-N-和端基异构体位置修饰，适合作为Lewis-x及相关化合物合成中间体的不同乳糖胺衍生物。并以奇异布拉氏菌中丰富的β-D-半乳糖苷酶为催化剂。因此，甲基O-β-D-吡喃半乳糖基-（1→4）-2-叠氮基-2-脱氧-β-D-吡喃葡萄糖苷，乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧- 2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷和乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧-2-（2,2,2-三氯乙氧基羰基氨基）-1-硫基-β -D-吡喃葡萄糖苷以基于添加的受体计算的20-40％的产率形成。不经色谱法（萃取/结晶步骤）分离出结晶形式的2-邻苯二甲酰亚胺基衍生物。三糖衍生物乙基O-β-D-吡喃半乳糖-（1→4）-O-β-D-吡喃半乳糖-（1→4）-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷也孤立。对应

  DOI：

  10.1080/07328309708007328

文献信息

• Glycosidase-catalysed synthesis of di- and trisaccharide derivatives related to antigens involved in the hyperacure rejection of xenotransplants
  作者：Kurt G.I. Nilsson

  DOI：10.1016/s0040-4039(96)02235-6

  日期：1997.1

  A convenient enzymatic procedure, suitable for large scale preparation of the beta-thioethyl 2-N-Teoc-derivative of Ga1 alpha 1-3Gal beta 1-4GlcNAc, GalS1-4GlcNAc, is described (Teoc = 2,2,2-trichloroethoxycarbonyl). beta-D-Galactosidase from Bullera singularis was used for the specific synthesis of Gal beta 1-4GlcNTeoc beta-SEt from lactose and D-GlcNTeoc beta-SEt. alpha-D-Galactosidase from coffee beans was used for the stereo- specific and highly regioselective preparation of Gal alpha 1-3Gal beta 1-4GlcNTeoc beta-SEt, employing D-Gal alpha-OPhNO(2)-p as glycosyl donor and Gal beta 1-4GlcNTeoc beta-SEt as acceptor. Copyright (C) 1996 Elsevier Science Ltd
• Syntheses of Modified Carbohydrates with Glycosidases: Stereo- and Regiospecific Syntheses of Lactosamine Derivatives and Related Compounds¹
  作者：Kurt G.I. Nilsson、Hefeng Pan、Ulla Larsson-Lorek

  DOI：10.1080/07328309708007328

  日期：1997.5

  Abstract Different lactosamine derivatives, modified in the 2-N- and anomeric positions and suitable as intermediates for synthesis of Lewis-x and related compounds, were prepared with high specificity on a multigram scale directly from lactose, employing different D-glucosamine derivatives as acceptors and the abundant β-D-galactosidase from Bullera singularis as catalyst. Thus, methyl O-β-D-gala

  摘要以不同的D-葡萄糖胺衍生物为接受剂，直接从乳糖以高克数级制备了在2-N-和端基异构体位置修饰，适合作为Lewis-x及相关化合物合成中间体的不同乳糖胺衍生物。并以奇异布拉氏菌中丰富的β-D-半乳糖苷酶为催化剂。因此，甲基O-β-D-吡喃半乳糖基-（1→4）-2-叠氮基-2-脱氧-β-D-吡喃葡萄糖苷，乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧- 2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷和乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧-2-（2,2,2-三氯乙氧基羰基氨基）-1-硫基-β -D-吡喃葡萄糖苷以基于添加的受体计算的20-40％的产率形成。不经色谱法（萃取/结晶步骤）分离出结晶形式的2-邻苯二甲酰亚胺基衍生物。三糖衍生物乙基O-β-D-吡喃半乳糖-（1→4）-O-β-D-吡喃半乳糖-（1→4）-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷也孤立。对应