3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide | 3068-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide
• 英文别名: 3,4,6-Tri-O-acetyl-2-(2,4-dinitrophenyl)amino-2-deoxy-α-D-glucopyranosyl bromide；3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl bromide；3,4,6-tri-O-acetyl-2-(2,4-dinitroanilino)-2-deoxy-α-D-glucopyranosyl bromide；3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucosyl bromide；tri-O-acetyl-2-(2,4-dinitro-anilino)-2-deoxy-α-D-glucopyranosyl bromide；Tri-O-acetyl-2-(2,4-dinitro-anilino)-2-desoxy-α-D-glucopyranosylbromid；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(2,4-dinitroanilino)oxan-2-yl]methyl acetate
• CAS: 3068-36-8
• 化学式: C₁₈H₂₀BrN₃O₁₁
• 分子量: 534.274
• InChiKey: UEYBDGITNGDJHD-ZKXLYKBJSA-N

物化性质

• 熔点：
  162-164 °C
• 沸点：
  622.2±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide 在 吡啶 、 丙酮 作用下， 生成 methyl-[tri-O-acetyl-2-(2,4-dinitro-anilino)-2-deoxy-α-D-glucopyranoside]
  参考文献：
  名称：

  Wang; Tai, Huaxue Xuebao/Acta Chimica Sinica, 1958, vol. 24, p. 368,372; engl. Ref. S. 375

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4,6-Tetra-O-acetyl-2-(2,4-dinitroanilino)-2-desoxy-β-D-glucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Lloyd; Stacey, Chemistry and industry, 1955, p. 917

  摘要：

  DOI：
• 作为试剂：
  描述：

  2,3,4,6-tetra-O-(p-chlorobenzyl)-α-D-mannopyranoside 在 三苄胺 、 sodium methylate 、 silver perchlorate 、 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  α-D-吡喃半乳糖基和α-D-吡喃甘露糖基2-氨基-2-脱氧-α-D-吡喃葡萄糖苷的合成及其糖苷键的构象

  摘要：

  海藻胺的新类似物α-D-吡喃半乳糖基2-氨基-2-脱氧-α-D-吡喃葡萄糖苷通过2,3,4,6-四-O-(对氯苄基)-α的糖基化合成-D-吡喃半乳糖与 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilinino)-α-D-glupyranosyl bromide，在苯中使用高氯酸银和三苄胺，然后进行色谱分离以及随后去除保护基团。类似地，合成了α-D-吡喃甘露糖基2-氨基-2-脱氧-α-D-吡喃葡萄糖苷。这些 α,α-二糖的糖苷键的构象与它们异头碳的 13C 化学位移有关。

  DOI：

  10.1246/bcsj.54.2728

文献信息

• Benzyl Derivatives of<b><i>N</i></b>-2,4-Dinitrophenyl-<b>D</b>-glucosamine and Their Use for Oligosaccharide Synthesis
  作者：Shinkiti Koto、Motoko Hirooka、Kazuo Yago、Mitsuo Komiya、Toshio Shimizu、Kumi Kato、Tsunehiko Takehara、Ayami Ikefuji、Ayako Iwasa、Saho Hagino、Michiyo Sekiya、Yozo Nakase、Shonosuke Zen、Fumiya Tomonaga、Shigehiko Shimada

  DOI：10.1246/bcsj.73.173

  日期：2000.1

  Four tri-O-benzyl derivatives of 2-deoxy-2-(2,4-dinitroanilino)-D-glucopyranose were synthesized. Glycosylation using 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-D-glucopyranose as glycosyl donor and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine produced β-glycosides with complete selectivity. Starting from benzyl 3,6-di-O-benzyl-2-deoxy-2-(2

  合成了 2-脱氧-2-(2,4-二硝基苯胺)-D-吡喃葡萄糖的四种三-O-苄基衍生物。使用 3,4,6-三-O-苄基-2-脱氧-2-(2,4-二硝基苯胺)-D-吡喃葡萄糖作为糖基供体和对硝基苯磺酰氯、三氟甲磺酸银和三乙胺的试剂混合物进行糖基化具有完全选择性的β-糖苷。以苄基 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-吡喃葡萄糖苷为受体，O-α-D-吡喃半乳糖基-(1→4)-O -β-D-吡喃半乳糖基-(1→4)-2-乙酰氨基-2-脱氧-D-吡喃葡萄糖，人类血型P1-抗原决定簇，被合成。
• SYNTHESIS OF RIBOSTAMYCIN. AN APPLICATION OF A CHEMICAL CONVERSION METHOD FROM CARBOHYDRATE TO AMINOCYCLITOL
  作者：Masayuki Yoshikawa、Yoshiharu Ikeda、Kohei Takenaka、Masahiro Torihara、Isao Kitagawa

  DOI：10.1246/cl.1984.2097

  日期：1984.12.5

  An aminoglycoside antibiotic ribostamycin was synthesized from D-glucosamine and ribose via an amino-trisaccharide intermediate, which was prepared through successive selective glycosidations on the 1,6-anhydro-D-glucosamine moiety.

  氨基糖苷类抗生素核糖霉素是由 D-葡糖胺和核糖通过氨基-三糖中间体合成的，该中间体是通过对 1,6-脱水-D-葡糖胺部分的连续选择性糖苷化制备的。
• Semisynthetic aminoglycoside antibacterials. Part 7. Synthesis of novel hexopyranosyl and hexofuranosyl derivatives of gentamine C1 and C1a
  作者：Peter J. L. Daniels、Charles E. Luce、Alan K. Mallams、James B. Morton、Surinderjit S. Saluja、Hsingan Tsai、Jay Weinstein、John J. Wright、George Detre、Masato Tanabe、Dennis M. Yasuda

  DOI：10.1039/p19810002137

  日期：——

  Acidic hydrolysis of gentamicin C1 and C1a provides ready access to the pseudodisaccharides gentamine C1 and C1a respectively. Glycosylation of tetrakis-N-benzyloxycarbonylgentamine C1 and C1a using the Koenigs–Knorr or Lemieux–Nagabhushan reactions has led to the preparation of a series of novel 6-O-α- and -β-3-amino-3-deoxy- and 2-amino-2-deoxy-D-hexopyranosyl and hexofuranosyl analogues of the gentamicins

  庆大霉素C 1和C 1a的酸性水解可分别轻松获得假二糖gentamine C 1和C 1a。使用Koenigs-Knorr或Lemieux-Nagabhushan反应的四-N-苄氧基羰基银胺C 1和C 1a的糖基化反应导致制备了一系列新型的6 - O -α-和-β-3-氨基-3-脱氧-庆大霉素的2-氨基-2-脱氧-D-己吡喃糖基和己呋喃糖基类似物。的13 C NMR代表性化合物的性质所描述和有关C-4-旋转异构体群体ö和C-6- Ò 糖苷键进行了讨论。
• Chemical modification of validamycin A.
  作者：Akira HASEGAWA、Toshiyuki KOBAYASHI、Hideyuki HIBINO、Makoto KISO

  DOI：10.1271/bbb1961.44.143

  日期：——

  The chemical modification of validamycin A was examined. One of the synthetic validamy-cin analogs, N[(1S)-(1, 4, 6/5)-4, 5, 6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl] [O-β-2-amino-2-deoxy-D-glucopyranosyl-(1→3)-(1S)-(1, 2, 4/3, 5) -2, 3, 4- trihydroxy-5-hydroxymethyl-cyclohexy] amine monohydrochloride had almost the same activity against the sheath blight of rice plants as that of validamycin A. Partial synthesis of validamycin A was also examined.

  检查了井冈霉素 A 的化学修饰。一种合成的有效霉素类似物，N[(1S)-(1, 4, 6/5)-4, 5, 6-三羟基-3-羟甲基-2-环己烯基] [O-β-2-氨基- 2-脱氧-D-吡喃葡萄糖基-(1→3)-(1S)-(1, 2, 4/3, 5) -2, 3, 4-三羟基-5-羟甲基-环己基]胺单盐酸盐几乎相同对抗水稻纹枯病的活性与井冈霉素A的活性相同。还检测了井冈霉素A的部分合成。
• SYNTHESIS OF 2-AMINO-2-DEOXY-α-D-GLUCOPYRANOSYL β-D-FRUCTOFURANOSIDE (2-AMINO-2-DEOXY-SUCROSE
  作者：Shinkiti Koto、Shigeru Inada、Shonosuke Zen

  DOI：10.1246/cl.1980.183

  日期：1980.2.5

  2-Amino-2-deoxy-α-d-glucopyranosyl β-d-fructofuranoside (2-amino-2-deoxy-sucrose) was synthesized by condensation of 3,4,6-tri-O-acetyl-2-(2,4-dinitroanilino)-2-deoxy-α-d-glucopyranosyl bromide and 1,3,4,6-tetra-O-benzyl-d-fructofuranose with the aid of silver perchlorate and tribenzylamine in benzene, followed by removal of protecting groups.

  2-氨基-2-脱氧-α-d-吡喃葡萄糖基β-d-呋喃果糖苷（2-氨基-2-脱氧-蔗糖）通过3,4,6-三-O-乙酰基-2-(2 ,4-二硝基苯胺基)-2-脱氧-α-d-吡喃葡萄糖基溴和1,3,4,6-四-O-苄基-d-呋喃果糖在高氯酸银和三苯胺的苯溶液中反应，然后除去保护层组。