1,2-O-isopropylidene-α-D-galactofuranose | 51921-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-α-D-galactofuranose
• 英文别名: 1,2-O-Isopropyliden-α-D-galactofuranose；1.2-O-Isopropyliden-α-D-galactofuranose；(1R)-1-[(3Ar,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 51921-42-7
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: BGGCXQKYCBBHAH-DWOUCZDBSA-N

物化性质

• 沸点：
  422.4±40.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-D-galactofuranose 在 palladium on activated charcoal 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氢氧化钾 、 sodium periodate 、 正丁基锂 、 三氯异氰尿酸 、 camphor-10-sulfonic acid 、 水 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 β-D-[1-13C]galactofuranose
  参考文献：
  名称：

  Practical synthesis of [1-13C]- and [6-13C]-d-galactose

  摘要：

  The chemical synthesis of C-13-labeled D-galactose as useful molecular probes for studying the conformation of oligosaccharides attached to proteins was performed. The method for synthesizing the title labeled compounds was newly developed via the corresponding 1-ene and 5-ene compounds derived from 1,2:5,6-di-O-isoproppylidene-alpha-D-galactofuranose by considering the efficient introduction of the atom. All protons of galactose from H-1 to H-6 were observed by the HMQC-HOHAHA technique using 1:1 mixtures of methyl [1-C-13]- and [6-C-13]-beta-D-galactopyranoside, which were prepared from the title compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01098-0
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 sodium hydroxide 、 硼烷 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 1,2-O-isopropylidene-α-D-galactofuranose
  参考文献：
  名称：

  Practical synthesis of [1-13C]- and [6-13C]-d-galactose

  摘要：

  The chemical synthesis of C-13-labeled D-galactose as useful molecular probes for studying the conformation of oligosaccharides attached to proteins was performed. The method for synthesizing the title labeled compounds was newly developed via the corresponding 1-ene and 5-ene compounds derived from 1,2:5,6-di-O-isoproppylidene-alpha-D-galactofuranose by considering the efficient introduction of the atom. All protons of galactose from H-1 to H-6 were observed by the HMQC-HOHAHA technique using 1:1 mixtures of methyl [1-C-13]- and [6-C-13]-beta-D-galactopyranoside, which were prepared from the title compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01098-0

文献信息

• A Simple and Facile Chemo- and Regioselective Deprotection of Acetonides Using Silica Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst
  作者：G. Mahender、R. Ramu、C. Ramesh、Biswanath Das

  DOI：10.1246/cl.2003.734

  日期：2003.8

  Silica supported sodium hydrogen sulfate (NaHSO4·SiO2) has been found to be an efficient heterogeneous catalyst for chemo- and regioselective deprotection of acetonides at room temperature to produce the corresponding diols in excellent yields.

  已发现二氧化硅负载的硫酸氢钠 (NaHSO4·SiO2) 是一种有效的多相催化剂，可用于在室温下对丙酮化物进行化学和区域选择性脱保护，以优异的产率生产相应的二醇。
• Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants
  作者：Shilpi Gupta、Smritilekha Bera、Dhananjoy Mondal

  DOI：10.1021/acs.joc.9b02561

  日期：2020.2.21

  the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。
• MUKHERJEE, ATREYEE;ROY, NIRMOLENDU, INDIAN J. CHEM. B, 27,(1988) N1, C. 1037-1038
  作者：MUKHERJEE, ATREYEE、ROY, NIRMOLENDU

  DOI：——

  日期：——
• HORI, HIROSHI;NISHIDA, YOSHIHIRO;OHRUI, HIROSHI;MEGURO, HIROSHI, J. ORG. CHEM., 54,(1989) N, C. 1346-1353
  作者：HORI, HIROSHI、NISHIDA, YOSHIHIRO、OHRUI, HIROSHI、MEGURO, HIROSHI

  DOI：——

  日期：——
• FELDMAN, D. P.;VOJTENKO, A. D.;SHIMANSKAYA, M. V.;LIDAK, M. YU., XIM.-FARMATS. ZH., 23,(1989) N, S. 326-328
  作者：FELDMAN, D. P.、VOJTENKO, A. D.、SHIMANSKAYA, M. V.、LIDAK, M. YU.

  DOI：——

  日期：——