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 | 68733-13-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 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
• 英文别名: 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-β-D-glucopyranosyl nitrate；3,6-Di-O-acetyl-2-azido-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylnitrat；[(2R,3S,4R,5R,6S)-4-acetyloxy-5-azido-6-nitrooxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68733-13-1
• 化学式: C₂₄H₃₂N₄O₁₈
• 分子量: 664.534
• InChiKey: MBFAYVBABZZODL-FHKWVZCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  255
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  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 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  hexa-O-acetyl-D-lactal 生成 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
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Use of Hydrazine Acetate as a Mild and Efficient Reagent for Anomeric Denitration of Carbohydrates
  作者：Tatsushi Toyokuni、Shaopei Cai、Barbara Dean

  DOI：10.1055/s-1992-26347

  日期：——

  Treatment of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α,β-D-galactopyranosyl nitrate (1), 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4, 6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranosyl nitrate (3), and 6-O-acetyl-2-azido-2-deoxy-3,4-O-isopropylidene-α,β-D-galactopyranosyl nitrate (5) with a slight excess of hydrazine acetate in anhydrous dimethylformamide at room temperature for 2 hours gave the corresponding hemiacetals, 2, 4, and 6 in the range of an 87-92 % yield.

  将 3,4,6-三-O-乙酰基-2-叠氮-2-脱氧-δ±,δ-D-吡喃半乳糖硝酸酯 (1)、3,6-二-O-乙酰基-2-叠氮-2-脱氧-4-O-(2,3,4, 6-四-O-乙酰基-δ-D-吡喃半乳糖基)-δ±,δ-D-吡喃葡萄糖硝酸酯 (3) 和 6-O-乙酰基-2-叠氮-2-脱氧-3、在室温下，在无水二甲基甲酰胺中加入稍过量的乙酸肼 2 小时，再加入 4-O-异亚丙基-δ,δ-D-吡喃半乳糖基硝酸酯（5），得到相应的半乙酸酯 2、4 和 6，收率范围为 87-92%。
• Synthesis of 5′-O-(2-Azido-2-deoxy--D-glycosyl)nucleosides and Their Antitumor Activities
  作者：Gui-Sheng Zhang、Jie Chen、Ji-Mei Min、Li-He Zhang

  DOI：10.1002/hlca.200390163

  日期：2003.6

  corresponding α-D-glucopyranose-type glycosyl donor 9/10 reacted at room temperature with protected nucleosides 12–15 in CH2Cl2 solution in the presence of BF3⋅OEt2 as promoter to give 5′-O-(2-azido-2-deoxy-α-D-glycosyl)nucleosides in reasonable yields (Schemes 2 and 3). Only the 5′-O-(α-D-mannopyranosyl)nucleosides were obtained. Compounds 21, 28, 30, and 31 showed growth inhibition of HeLa cells and hepatoma

  1,3,4,6-四-O-乙酰基-2-叠氮基-2-脱氧-β -D-甘露吡喃糖（4）或1,3,6-三-O-乙酰基-2-叠氮基的混合物-2-脱氧-4- ö - （2,3,4,6-四ö乙酰基β -D-吡喃半乳糖基） - β -D-吡喃甘露糖（10）和相应的α -D-吡喃葡萄糖型的糖基供体9 / 10与受保护的核苷在室温下反应12 - 15在CH 2氯2在BF的存在溶液3 ⋅OEt 2作为启动子以合理的产率得到5'- O-（2-叠氮基-2-脱氧-α -D-糖基）核苷（方案2和3）。仅获得5'- O-（α -D-甘露吡喃糖基）核苷。化合物21、28、30和31在体外以10μM的浓度显示出对HeLa细胞和肝癌Bel-7402细胞的生长抑制作用。
• Synthesis of hepta- and penta-saccharides, part of the complex-type carbohydrate portion of glycoproteins
  作者：Jan Arnarp、Jörgen Lönngren

  DOI：10.1039/c39800001000

  日期：——

  Silver trifluoromethanesulphonate-promoted condensation of 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-mannopyranoside and benzyl 2,4-di-O-benzyl-3,6-di-O-(3,4,6,-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside gave a protected pentasaccharide and a protected heptasaccharide in 56% and 43% yield, respectively; after deblocking the free penta- and

  三氟甲磺酸银促进的3,6-二-O-乙酰基-4- O-（2,3,4,6-四-O-乙酰基-β - D-吡喃半乳糖基）-2-脱氧-2-邻苯二甲酰亚胺基-缩合反应β - d -mannopyranoside和苄基2,4-二- ø -苄基-3,6-二- ö - （3,4,6， -三- ö苄基α - d -mannopyranosyl） - α - d -甘露糖吡喃糖苷以56％和43％的产率得到被保护的五糖和被保护的七糖。解封后，得到游离的五糖和七糖。
• 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，
• Synthesis of a tri-, a penta-, and a hepta-saccharide containing terminal N-acetyl-β-<scp>D</scp>-lactosaminyl residues, part of the ‘complex-type’ carbohydrate moiety of glycoproteins
  作者：Jan Arnarp、Jörgen Lönngren

  DOI：10.1039/p19810002070

  日期：——

  Silver trifluoromethanesulphonate-promoted condensation of 3,6-di-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide with benzyl 3-O-benzyl-4,6-O-benzyl-idene-α-D-mannopyranoside, benzyl 3,6-di-O-benzyl-α-D-mannopyranoside, and benzyl 3,6-di-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside gave the protected tri-, penta-, and

  三氟甲磺酸银促进的3,6-二-O-（2,3,4,6-四-O-乙酰基-β - D-吡喃半乳糖基）-2-脱氧-2-邻苯二甲酰亚胺-β - D-吡喃葡萄糖基溴的缩合反应用苄基3- ö -苄基-4,6- ö苄基偏二-α- d -mannopyranoside，苄基3,6-二- ö苄基α- d -mannopyranoside，和苄基3,6-二- ö -（3,4,6-三-O-苄基-α - D-甘露吡喃糖基）-2,4-二-O-苄基-α - Dβ-甘露糖吡喃糖苷分别以66％，72％和56％的收率得到了受保护的三糖，五糖和七糖衍生物。将2-脱氧-2-邻苯二甲酰亚胺基团交换成2-乙酰氨基-2-脱氧基团并解封后，获得了游离的寡糖。