1,2:5,6-di-O-isopropylidene-3-O-trityl-α-D-glucofuranose | 63096-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-O-trityl-α-D-glucofuranose
• 英文别名: O¹,O²;O⁵,O⁶-diisopropylidene-O³-trityl-α-D-glucofuranose；O¹,O²;O⁵,O⁶-Diisopropyliden-O³-trityl-α-D-glucofuranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-trityloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 63096-92-4
• 化学式: C₃₁H₃₄O₆
• 分子量: 502.607
• InChiKey: YFDJJECJIXYTCP-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(3aR,5S,6S,7R,7aR)-7-acetyloxy-2-ethylsulfanyl-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] acetate 、 1,2:5,6-di-O-isopropylidene-3-O-trityl-α-D-glucofuranose 在 triphenylmethyl perchlorate 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到Acetic acid (2S,3R,4S,5R,6S)-4,5-diacetoxy-2-[(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-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters

  摘要：

  DOI：

  10.1016/s0008-6215(00)84672-8
• 作为产物：
  描述：

  双丙酮葡萄糖 生成 1,2:5,6-di-O-isopropylidene-3-O-trityl-α-D-glucofuranose
  参考文献：
  名称：

  GIGG, JILL;GIGG, ROY;PAYNE, SHEILA;CONANT, ROBERT, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 8, 1757-1762

  摘要：

  DOI：

文献信息

• Novel Selectivity in Carbohydrate Reactions, IV: DABCO-Mediated Regioselective Primary Hydroxyl Protection of Carbohydrates
  作者：Bharat Kacheshwar Gadakh、Premanand Ramrao Patil、Satish Malik、K. P. Ravindranathan Kartha

  DOI：10.1080/00397910802656067

  日期：2009.6.9

  Abstract An efficient procedure for the regioselective tritylation of primary hydroxyl group of aldohexopyranosides and nucleosides using trityl chloride in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in dichloromethane has been developed. Subsequent acetylation of the tritylated products in the same pot has been made possible, thereby providing an efficient route to the fully protected carbohydrate

  摘要 已开发出一种在二氯甲烷中 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 存在下使用三苯甲基氯对醛己糖苷和核苷的伯羟基进行区域选择性三苯甲基化的有效方法。在同一个锅中三苯甲基化产物的后续乙酰化已经成为可能，从而为完全保护的碳水化合物衍生物提供了一种有效的途径，可以化学选择性地加以区分。
• The allyl group for protection in carbohydrate chemistry. Part 20. Synthesis of 1<scp>L</scp>-1-O-methyl-myo-inositol [(+)-bornesitol] by resolution of (±)-1,2,4-tri-O-benzyl-myo-inositol
  作者：Jill Gigg、Roy Gigg、Sheila Payne、Robert Conant

  DOI：10.1039/p19870001757

  日期：——

  acetic anhydride-dimethyl sulphoxide gave the corresponding ketones, which were reduced with sodium borohydride to give the starting alcohols in good yield, thus providing suitable routes for the synthesis of isotopically labelled material. Racemic 1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol was resolved using (–)-ω-camphanic acid chloride to give, readily and in high yield (86%), the ω-camphanate

  外消旋1,2,4-三-O-苄基-肌醇肌醇，由（±）-1,4-二-O-苄基-5,6-O-异亚丙基制备的由两个新的路线肌醇肌醇，一个途径涉及结晶中间体（±）-1 - O-烯丙基-3，6-二-O-苄基-4，5- O-异亚丙基-肌醇。后者和（±）氧化-1,2,4-三-O-苄基-5,6-O-异亚丙基肌醇肌醇与乙酸酐-二甲亚砜，得到相应的酮，将其用硼氢化钠还原以高收率得到起始醇，从而为合成同位素标记的物质提供了合适的途径。外消旋1,2,4-三-O-苄基-5,6- O-异亚丙基-肌（ - ） -肌醇用解决ω-樟脑酰氯，得到，容易地和高产率（86％），1的ω-莰烷d -1,2,4-三ø -苄基-5， 6- ø异亚丙基肌肉肌醇，将其转化成1-大号-1- ö甲基肌醇肌醇[（+） -甲基肌醇]和1 d -1,2,4,5,6-五ø -苄基-肌醇已预先通过perbenzylated肌醇半乳糖苷的水解而获得的肌醇。
• The Rates of Reaction of Diacetone Glucose, Diacetone Galactose and Diacetone Sorbose with Triphenylchloromethane in Pyridine Solution¹
  作者：R. C. Hockett、H. G. Fletcher、J. B. Ames

  DOI：10.1021/ja01854a060

  日期：1941.9