O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide | 68733-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide
• 英文别名: 1-bromo-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranoside；3,6-Di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-desoxy-α-D-glucopyranosylbromid；3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosyl bromide；3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl bromide；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-5-azido-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68733-24-4
• 化学式: C₂₄H₃₂BrN₃O₁₅
• 分子量: 682.433
• InChiKey: SRHWZINJYAFHTJ-FHKWVZCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide 在 calcium sulfate 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 25.0h， 生成 methyl O-β-D-galactopyranosyl-(1-4)-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Wong, Ting C.; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 1207 - 1213

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl nitrate 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  LEMIEUX, R. U.;RATCLIFFE, R. M.

  摘要：

  DOI：

文献信息

• Regioselektive glycosylierung an stellungen 3′ und 4′ von lactose-derivaten
  作者：Hans Paulsen、Klaus-Michael Steiger

  DOI：10.1016/0008-6215(87)80245-8

  日期：1987.11

  Abstract Derivatives of lactose, unsubstituted at OH-3′ and OH-4′, were glycosylated regioselectively depending on the catalyst. In a heterogeneous system with silver silicate as catalyst, glycosylation at OH-4′ was favored, whereas in a homogeneous system with silver triflate as catalyst, a favored glycosylation at OH-3′ was observed. Thus, the tetrasaccharides, O -β- D -galactopyranosyl-(1→4)- O

  摘要依赖于催化剂，在OH-3'和OH-4'处未取代的乳糖衍生物被区域选择性地糖基化。在以硅酸银为催化剂的非均相体系中，在OH-4'处的糖基化是有利的，而在以三氟甲磺酸银为催化剂的均相系统中，在OH-3'处观察到了良好的糖基化。因此，四糖，O-β-D-吡喃半乳糖基-（1→4）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃吡喃糖基）-（1→4）-O-β-D-吡喃半乳糖基-（1→4）-D-吡喃葡萄糖和O-β-D-吡喃半乳糖基-（1→4）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃吡喃糖基）-（1→3）-O -β-D-吡喃半乳糖基-（1→4）-D-吡喃葡萄糖和三糖O-（2-乙酰氨基-2-脱氧-β-D-吡喃半乳糖基）-（1→4）-O-β-D容易合成-半乳糖吡喃糖基-（1→4）-2-乙酰氨基-2-脱氧-D-吡喃葡萄糖。
• Synthese eines N-acetylneuraminsäure-haltigen syntheseblocks. Kupplung zum N-acetylneuraminsäuretetrasaccharid mit trimethylsilyltriflat
  作者：Hans Paulsen、Holger Tietz

  DOI：10.1016/s0008-6215(00)90670-0

  日期：1985.12

  Abstract A trisaccharide synthetic block consisting of N -acetylneuraminic acid and lactosamine that allows general coupling reactions to other saccharide units was obtained. O -(Methyl 5-acetamido-4,7,8,9-tetra- O -acetyl-3,5-dideoxy-α- and -β- d - glycero - d - galacto -2-nonulopyranosylonate)-(2→6)- O -(2,3,4-tri- O -acetyl-β- d -galactopyranosyl)-(1→4)-1,3,6-tri- O -acetyl-2-desoxy-2-phthalimido-β-

  摘要获得了由N-乙酰神经氨酸和乳糖胺组成的三糖合成嵌段，该嵌段可与其他糖单元进行一般偶联反应。O-（5-乙酰氨基-4,7,8,9-四-甲基-O-乙酰基-3,5-二脱氧-α-和-β-d-甘油-d-半乳清-2-壬基吡喃二磺酸酯）-（2→ 6）-O-（2,3,4-三-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-1,3,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖被用作糖基供体。在三甲基甲硅烷基三氟甲基磺酸盐的存在下，通过与在OH-2处代表糖基受体的未取代的d-甘露糖衍生物反应，将两种化合物转化为四糖。除去保护基团得到O-（5-乙酰氨基-3，
• Synthese eines trisaccharides aus N-acetylneuraminsäure und N-acetyllactosamin
  作者：Hans Paulsen、Holger Tietz

  DOI：10.1016/0008-6215(84)85141-1

  日期：1984.1

  -galactopyranosyl)-β- d -glucopyranoside in the presence of mercury cyanide—mercury bromide gave a 1:1 mixture of the two anomeric (2→6)-linked trisaccharides containing N-acetylneuraminic acid. By chromatography, 22% of benzyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy- d -glycero-α- d -galacto-2- nonulopyranosylonate)-(2→6)-O-(2,3-di-O-benzyl-β- d -galactopyranosyl)-(1→4)-2-azido-3,6-d

  摘要5-乙酰氨基-4,7,8,9-四-O-乙酰基-2-氯-2,3,5-三脱氧-d-甘油-β-d-半乳糖-2-壬基吡喃磺酸根的反应在存在下用苄基2-叠氮基-3,6-二-O-苄基-2-脱氧-4-O-（2,3-二-O-苄基-β-d-吡喃半乳糖基）-β-d-吡喃葡萄糖苷氰化汞-溴化汞的分离得到了两个含有N-乙酰神经氨酸的异头（2→6）连接的三糖的1：1混合物。通过色谱法，得到22％的苄基O-（甲基5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-d-甘油-α-d-半乳糖-2-壬基吡喃二磺酸根）- （2→6）-O-（2,3-二-O-苄基-β-d-吡喃半乳糖基）-（1→4）-2-叠氮基-3,6-二-O-苄基-2-脱氧-可以分离出β-d-吡喃葡萄糖苷和23％的相应β-（2→6）连接的异构体。解封序列，包括硫化氢还原，乙酰化，脱乙酰化，酯水解，
• Syntheses of derivatives of <i>N</i>-acetyl-<scp>D</scp>-lactosamine from <scp>D</scp>-lactal hexaacetate. Hexa-<i>O</i>-acetyl-2-deoxy-2-phthalimido-β-<scp>D</scp>-lactosyl chloride
  作者：R. U. Lemieux、S. Z. Abbas、M. H. Burzynska、R. M. Ratcliffe

  DOI：10.1139/v82-011

  日期：1982.1.1

  Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride (7) from lactal hexaacetate (1). One route involves, in the first stage, reaction ...

  提出了两种反应路线，用于从乳酸六乙酸酯 (1) 制备六-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-乳糖酰氯 (7)。一个途径涉及，在第一阶段，反应......
• Synthesis and potential antimetastatic activity of monovalent and divalent β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-d-glucopyranosides
  作者：Qing Li、Bin Su、Hui Li、Xiang-Bao Meng、Meng-Shen Cai、Zhong-Jun Li、Rou-Li Zhou、Ta-Lin Suo

  DOI：10.1016/s0008-6215(02)00438-x

  日期：2003.1

  Anomers of monovalent and divalent beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-gluco-pyranosides were synthesized under different glycosylation conditions, and evaluated for in vitro antimetastatic activity. Three compounds showed promising inhibitory effects on cancer cell attachment, spreading, migration, and invasion. (C) 2002 Elsevier Science Ltd. All rights reserved.