3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose | 65434-49-3

• 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-O-isopropylidene-α-D-galactofuranose
• 英文别名: 3-O-benzyl-1,2-O-isopropylidene-β-L-indofuranose；(R)-1-((3AR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol；(1R)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 65434-49-3
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: CIFFIYJOTIJKSX-GZBLMMOJSA-N

物化性质

• 沸点：
  460.4±45.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 在 palladium on activated charcoal 、 镍 sodium periodate 、 正丁基锂 、 jones' reagent 、 Collins oxidation agent 、 硫酸 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 16.25h， 生成 (3aR,4S,6aR)-4-octyldihydrofuro[3,4-b]furan-2,6(3H,6aH)-dione
  参考文献：
  名称：

  Synthesis of bis-.gamma.-lactones from "diacetone glucose". 4. Optically active avenaciolide and isoavenaciolide

  摘要：

  DOI：

  10.1021/jo00224a025
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 硼烷 、 水 、 sodium hydride 、 溶剂黄146 、 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-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。
• Branched-chain Sugars. XXI. Synthesis of New Branched-chain Cyclitols Having<i>neo</i>-,<i>myo</i>-, and<i>chiro</i>-Configurations from 3-<i>O</i>-Benzyl-5,6-dideoxy-5-<i>C</i>-(1,3-dithian-2-yl)-6-nitro-D-galactofuranose and -L-altrofuranose
  作者：Masaharu Iwakawa、Juji Yoshimura、Masuo Funabash

  DOI：10.1246/bcsj.54.496

  日期：1981.2

  intra-molecular cyclization under weakly basic conditions afforded a mixture of branched-chain cyclitols having neo-, myo-, and chiro-configuration. A similar cyclization of the O-deisopropylidenated product of 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-5-C-(nitromethyl)-β-L-arabino-hexofuranose also afforded a mixture of cyclitols having neo-, myo-, and chiro-configuration. The results confirm the importance

  2-lithio-1,3-dithiane 与 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-β-L-arabino-hex-5-enofuranose 的迈克尔加成得到a 1 : 1.8 3-O-苄基-5,6-二脱氧-5-C-(1,3-二噻烷-2-基)-1,2-O-异亚丙基-6-硝基-α-D-的混合物呋喃半乳糖和-β-L-呋喃糖。在弱碱性条件下去除异亚丙基和分子内环化得到具有新构型、肌构型和手性构型的支链环多醇的混合物。3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-5-C-(nitromethyl)-β-L-arabino-hexofuranose 的 O-deisopropidedenated 产物的类似环化也提供了具有新构型、肌构型和手性构型的环多醇混合物。结果证实了两个庞大基团的重要性，例如
• 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
• Ortho ester Claisen rearrangements of three 3-C-(hydroxymethyl)methylene derivatives of hexofuranose: stereoselective introduction of a quaternary center on C-3 of D-ribo-, L-lyxo-, and D-arabino-hexofuranoses
  作者：Kinichi Tadano、Yoko Idogaki、Hirohiko Yamada、Tetsuo Suami

  DOI：10.1021/jo00383a005

  日期：1987.4
• 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.