tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite | 10424-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite
• 英文别名: tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosido)phosphite；phosphorous acid tris-(O¹,O²;O⁵,O⁶-diisopropylidene-α-D-glucofuranose-3-yl ester)；Phosphorigsaeure-tris-(O¹,O²;O⁵,O⁶-diisopropyliden-α-D-glucofuranose-3-ylester)
• CAS: 10424-85-8
• 化学式: C₃₆H₅₇O₁₈P
• 分子量: 808.812
• InChiKey: ALQHZYOTDDLWNT-QDQMEFFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  55.0
• 可旋转键数：
  9.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  166.14
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite 在 水 作用下， 生成 ((S)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester
  参考文献：
  名称：

  Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds

  摘要：

  Chiral symmetric di- and trialkylphosphites, derivatives of (-)-borneol, (-)-menthol and (-)-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, were studied as starting reagents for the preparation of chiral organophosphorus compounds. The reaction occurs by asymmetric induction at the alpha-carbon atom of substituted alpha-alkylphosphonates. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions. The configuration of the alkylphosphonates was established by NMR spectroscopy, by transformation into alpha-hydroxyalkylphosphonic acids and by X-ray crystal structure analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00166-9
• 作为产物：
  描述：

  Lithium; (3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-olate 在 三氯化磷 作用下， 以 乙醚 为溶剂， 以90.2%的产率得到tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite
  参考文献：
  名称：

  Stolmar, Matthias; Floriani, Carlo; Gervasio, Giuliana, Journal of the Chemical Society, Dalton Transactions, 1997, p. 1119 - 1122

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites
  作者：O. I. Kolodiazhnyi、E. V. Grishkun、S. Sheiko、O. Demchuk、H. Thoennessen、P. Jones、R. Schmutzler

  DOI：10.1007/bf02496414

  日期：1999.8

  Chiral C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites, derived from (−)-borneol, (−)-menthol, and 1,2∶5,6-di-O-isopropylidene-α-d-glucofuranose, were studied as the starting reagents for the preparation of chiral organophosphorus compounds. The reactions of C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied

  研究了衍生自 (-)-冰片、(-)-薄荷醇和 1,2∶5,6-二-O-异亚丙基-α-d-呋喃葡萄糖的手性 C2-对称二烷基亚磷酸酯和 C3-对称三烷基亚磷酸酯作为制备手性有机磷化合物的起始试剂。C2-对称亚磷酸二烷基酯和 C3-对称亚磷酸三烷基酯与醛和胺或醛的反应伴随着在 α-碳原子上的不对称诱导，分别产生光学活性的 α-氨基烷基膦酸酯或 α-羟基烷基膦酸酯。反应的立体选择性取决于起始化合物的结构和反应条件。
• Reactions of Carbohydrates in Liquid Ammonia. II. Apparatus and Methods. Alkyl, Acyl and Certain Metallic and Non-metallic Derivatives of Diacetoneglucose
  作者：Irving E. Muskat

  DOI：10.1021/ja01326a071

  日期：1934.11
• Babiarz, Joseph E.; Pastor, Stephen D., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 91, # 1-4, p. 263 - 270
  作者：Babiarz, Joseph E.、Pastor, Stephen D.

  DOI：——

  日期：——