(1R,2R)-1,2-bis((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diyl dibenzoate | 96149-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-1,2-bis((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diyl dibenzoate
• 英文别名: 1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol-3,4-diyl dibenzoate；1,2-bis(2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diyl dibenzoate；[(1R,2R)-2-benzoyloxy-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl] benzoate
• CAS: 96149-47-2
• 化学式: C₂₆H₃₀O₈
• 分子量: 470.519
• InChiKey: BUABSGAEKGDYIC-GXRSIYKFSA-N

物化性质

• 熔点：
  82-85 °C
• 沸点：
  570.7±45.0 °C(predicted)
• 密度：
  1.198±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-bis((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diyl dibenzoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 草酰氯 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.75h， 生成 [(2R,3R,4R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-5-methyl-1,2-bis(phenylmethoxymethoxy)hex-5-en-3-yl] benzoate
  参考文献：
  名称：

  Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?

  摘要：

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.

  DOI：

  10.1021/jo961542v
• 作为产物：
  描述：

  甘露醇 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (1R,2R)-1,2-bis((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diyl dibenzoate
  参考文献：
  名称：

  Eldecalcitol 的高度立体选择性和可规模化合成

  摘要：

  发表于《国际有机制备和程序：有机合成新期刊》（第 56 卷，第 1 期，2024 年）

  DOI：

  10.1080/00304948.2023.2219200

文献信息

• Total Synthesis of (−)-Cleistenolide
  作者：Dokuburra Chanti Babu、Kankati Ashalatha、Chitturi Bhujanga Rao、Jon Paul Selvam Jondoss、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.201100086

  日期：2011.12

  AbstractAn efficient and short total synthesis of (−)‐cleistenolide (1) from D‐mannitol with an overall yield of 23.6% is described. The chiron approach for the synthesis of (−)‐cleistenolide involves a one‐C‐atom Wittig olefination, a selective allylic triethylsilyl protection, and a Grubbs‐catalyzed ring‐closure‐metathesis (RCM) reaction as the key steps.
• Synthesis of (3R,4R)-1,5-hexadien-3,4-diol and its unsymmetricalderivatives: Application to (R)-(+)-∝-lipoic acid
  作者：A.V.Rama Rao、S.V Mysorekar、M.K Gurjar、J.S Yadav

  DOI：10.1016/s0040-4039(00)96076-3

  日期：1987.1
• Studies directed toward the first total synthesis of acremodiol and acremonol
  作者：Gangavaram V.M. Sharma、Samala Mallesham、Chirutha Chandra Mouli

  DOI：10.1016/j.tetasy.2009.10.030

  日期：2009.11

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.
• A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4–SiO2
  作者：Hai-Xia Liu、Qin-Pei Wu、Yi-Nan Shu、Xi Chen、Xiao-Dong Xi、Ti-Jian Du、Qing-Shan Zhang

  DOI：10.1016/j.carres.2009.08.035

  日期：2009.11

  The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl beta-D-furanosides with a 2-acetoxyisopropyl group. (C) 2009 Elsevier Ltd. All rights reserved.
• Mulzer, Johann; Pietschmann, Catarina; Schoellhorn, Bernd, Liebigs Annalen, 1995, # 8, p. 1433 - 1440
  作者：Mulzer, Johann、Pietschmann, Catarina、Schoellhorn, Bernd、Buschmann, Juergen、Luger, Peter

  DOI：——

  日期：——