3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose | 65451-98-1

• 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: 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose
• 英文别名: (3aR,5S,6S,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-dihydro-5H-furo[3,2-d][1,3]dioxole；(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 65451-98-1
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: ZHFVGOMEUGAIJX-DRRXZNNHSA-N

物化性质

• 沸点：
  422.6±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 在 三氟乙酸 作用下， 反应 0.25h， 以1.5 g的产率得到3-O-benzyl-D-galactose
  参考文献：
  名称：

  2-取代的甲基α-d-吡喃半乳糖苷：对Griffonia simplicifolia I isolectins的A和B亚基的合成和结合亲和力

  摘要：

  N-乙酰基，N-三氟乙酰基，N-丙酰基，N-甲酰基，N-苯甲酰基，Np-硝基苯甲酰基，Np-氨基苯甲酰基和甲基-2-氨基-2-脱氧-α-甲基的N-甲基衍生物的结合亲和力已通过半乳甘露聚糖的半抗原抑制分析确定了D-半乳糖吡喃糖苷和Griffonia simplicifolia I isolectins的A和B亚基的甲基α-D-半乳糖吡喃糖苷的2-O-乙酰基，-苯甲酰基，-苄基和-甲基衍生物-isolectin沉淀系统。这些糖-蛋白质相互作用的模型与基于电子和空间效应的结果解释一起提供。

  DOI：

  10.1016/0008-6215(85)85047-3
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 硼烷 、 sodium hydride 、 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 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-benzyl-1,2:5,6-di-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。
• New Synthetic Approach to Protulactone A and Structural Analogues
  作者：Jovana Francuz、Sanja Djokić、Mirjana Popsavin、Marko V. Rodić、Vesna Kojić、Biljana Krüger、Velimir Popsavin

  DOI：10.1055/s-0042-1751400

  日期：——

  A new synthetic approach to protulactone A and several of its structural analogues, starting from d-galactose, has been developed. In a preliminary bioassay, all the compounds showed potent cytotoxicities. A structure–activity relationship analysis identified structural segments that are important for antiproliferative activity.

  protulactone A 及其几种结构类似物的新合成方法，从d-半乳糖，已经开发出来。在初步生物测定中，所有化合物都显示出强大的细胞毒性。结构-活性关系分析确定了对抗增殖活性重要的结构片段。
• Ruthenium tetraoxide phase-transfer-promoted oxidation of secondary alcohols to ketones
  作者：Philip E. Morris、Donald E. Kiely

  DOI：10.1021/jo00382a035

  日期：1987.3
• First synthesis of 5,6-branched galacto-hexasaccharide, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016
  作者：Guohua Zhang、Mingkun Fu、Jun Ning

  DOI：10.1016/j.tetasy.2004.12.014

  日期：2005.2

  alpha-D-Galactopyranosyl-(1 --> 6)-[beta-D-galactofuranosyl-(1 --> 5)]-beta-D-galactofuranosyl-(1 --> 6)-beta-D-galactofuranosyl-(1 --> 5)-[alpha-D -galactopyranosyl-(1 --> 6)]-beta-D-galactofuranose, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016, has been synthesized as its dodecyl glycoside 2 by coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranosyl trichloroacetimidate 14 with dodecyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranoside 16. The trisaccharide trichloroacetimidate donor 14 and trisaccharide acceptor 16 were regiospecifically prepared by employing 3-O-benzyl-1,2-O-isopropylidene-alpha-D-galactofuranose 4 as the glycosyl acceptor, and isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside 5 and 6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate 9 as glycosyl donors. (C) 2005 Elsevier Ltd. All rights reserved.
• Gurjar, M.K.; Devi, T. Rama; Reddy, K.L.N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 995 - 1003
  作者：Gurjar, M.K.、Devi, T. Rama、Reddy, K.L.N.、Sharma, P.A.、Dhar, T.G. Murali

  DOI：——

  日期：——