2,3,4-tri-O-benzoyl-α-D-glucopyranosyl tetramethylphosphoroamidate | 193953-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-α-D-glucopyranosyl tetramethylphosphoroamidate
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[bis(dimethylamino)phosphoryloxy]-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 193953-61-6
• 化学式: C₃₁H₃₅N₂O₁₀P
• 分子量: 626.6
• InChiKey: FOXDICUBDOHNQJ-HBXVOGJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-D-glucopyranosyl tetramethylphosphoroamidate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 丙腈 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  基于带有含磷离去基团的糖基供体和受体的寡糖合成

  摘要：

  通过利用糖基供体和带有含磷离去基团的受体之间的异头反应性的差异，开发了一种有效的寡糖合成策略，其中四甲基磷酸氨基甲酸酯基团作为异头保护基团和离去基团起着关键作用。

  DOI：

  10.1016/s0040-4039(97)01122-2
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 palladium dihydroxide 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙腈 为溶剂， 反应 54.0h， 生成 2,3,4-tri-O-benzoyl-α-D-glucopyranosyl tetramethylphosphoroamidate
  参考文献：
  名称：

  基于带有含磷离去基团的糖基供体和受体的寡糖合成

  摘要：

  通过利用糖基供体和带有含磷离去基团的受体之间的异头反应性的差异，开发了一种有效的寡糖合成策略，其中四甲基磷酸氨基甲酸酯基团作为异头保护基团和离去基团起着关键作用。

  DOI：

  10.1016/s0040-4039(97)01122-2

文献信息

• Direct and stereoselective synthesis of β-d-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor
  作者：Toshifumi Tsuda、Ryoichi Arihara、Shinya Sato、Miyuki Koshiba、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1016/j.tet.2005.08.090

  日期：2005.11

  A direct and practical method for the construction of β-mannosidic linkages is described. While β-selectivities in the TMSOTf-promoted glycosidation of 2,3,4,6-tetra-O-benzyl-d-mannosyl diethyl phosphite are found to be highly dependent on the reactivity of acceptor alcohols, 2,3-di-O-benzyl-4,6-O-benzylidene-d-mannosyl diethyl phosphite reacts with a wide range of acceptor alcohols in the presence

  描述了构建β-甘露糖苷键的直接和实用的方法。虽然发现在TMSOTf促进的2,3,4,6-四-O-苄基-d-甘露糖基亚磷酸二乙酯的糖基化反应中的β选择性高度依赖于受体醇的反应性，但2,3-二-O亚甲基-苄基-4,6- O-亚苄基-d-甘露糖基二乙基酯在TMSOTf存在下于-45°C在CH 2 Cl 2中与多种受体醇反应，以高收率得到β-甘露糖苷高β选择性。
• A stereocontrolled construction of 2-azido-2-deoxy-1,2-trans-β-glycosidic linkages utilizing 2-azido-2-deoxyglycopyranosyl diphenyl phosphates
  作者：Toshifumi Tsuda、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1016/s0040-4039(03)01557-0

  日期：2003.8

  A high-yielding and stereocontrolled construction of 2-azido-2-deoxy-1,2-trans-beta-glycosidic linkages has been achieved by exploiting TMSOTf-promoted 1,2-trans-glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates with various glycoside alcohols in propionitrile at -78degreesC. The present method exhibits the highest levels of 1,2-trans-beta-selectivity reported to date for this type of glycosidation. (C) 2003 Elsevier Ltd. All rights reserved.
• A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-d-glycosyl diphenyl phosphates as glycosyl donors
  作者：Toshifumi Tsuda、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1016/j.tet.2004.08.076

  日期：2004.11

  The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78 degreesC to afford 1,2-trans-beta-linked disaccharides in high yields with alpha:beta ratios ranging from 9:91 to 1: > 99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78 degreesC has proven to be among the best choice for the highest levels of beta-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for alpha-glycosyl-nitrilium ions over beta-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent beta-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.
• Tsuda, Toshifumi; Sato, Shinya; Nakamura, Seiichi, Heterocycles, 2003, vol. 59, # 2, p. 509 - 515
  作者：Tsuda, Toshifumi、Sato, Shinya、Nakamura, Seiichi、Hashimoto, Shunichi

  DOI：——

  日期：——
• Oligosaccharide synthesis based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups
  作者：Shun-ichi Hashimoto、Hiroki Sakamoto、Takeshi Honda、Shiro Ikegami

  DOI：10.1016/s0040-4039(97)01122-2

  日期：1997.7

  Efficient synthetic strategy for oligosaccharides has been developed by exploiting the difference in anomeric reactivity between glycosyl donors and acceptors carrying phosphorus-containing leaving groups, wherein the tetramethylphosphoroamidate group plays a pivotal role as anomeric protective group as well as leaving group.

  通过利用糖基供体和带有含磷离去基团的受体之间的异头反应性的差异，开发了一种有效的寡糖合成策略，其中四甲基磷酸氨基甲酸酯基团作为异头保护基团和离去基团起着关键作用。