Benzyl 2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside | 151266-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Benzyl 2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside
• 英文别名: benzyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside；2-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 151266-88-5
• 化学式: C₂₄H₂₅NO₇
• 分子量: 439.465
• InChiKey: BBCFNQSGIBWASF-MTSAVCEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl 2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 在 四丁基碘化铵 、 sodium hydride 、 一水合肼 、 溶剂黄146 、 三丁基氧化锡 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 Benzyl 3,6-di-O-benzyl-2-deoxy-2-amino-β-D-glucopyranoside
  参考文献：
  名称：

  Lafont, Dominique; Boullanger, Paul; Fenet, Bernard, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 565 - 584

  摘要：

  DOI：
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.5h， 生成 Benzyl 2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Lafont, Dominique; Boullanger, Paul; Fenet, Bernard, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 565 - 584

  摘要：

  DOI：

文献信息

• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
• Towards the chemoenzymatic synthesis of lipid A
  作者：Takeshi Sugai、Helena Ritzén、Chi-Huey Wong

  DOI：10.1016/s0957-4166(00)80153-6

  日期：1993.5

  New procedures have been developed for the synthesis of the two impotant components of lipid A; one is the lipase-catalyzed resolution of 3-hydrxytetradecanoic acid in tetrahydrofuran using vinyl acetate and the other is the synthesis of the disaccharide moiety using glycosylphosphite as the glycosylating reagent.
• Lafont, Dominique; Boullanger, Paul; Fenet, Bernard, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 565 - 584
  作者：Lafont, Dominique、Boullanger, Paul、Fenet, Bernard

  DOI：——

  日期：——