1,2:5,6-di-O-isopropylidene-α-D-galactofuranose | 10368-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose
• 英文别名: 1,2,5,6-di-O-isopropylidene-D-galactofuranose；1,2:5,6-Di-o-isopropylidene-alpha-d-galactofuranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 10368-86-2
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: KEJGAYKWRDILTF-SOYHJAILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 在 三氟甲磺酸三甲基硅酯 吡啶 、 MS 4 Angstroem 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-5,6-di-O-acetyl-1,2-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella

  摘要：

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00076-4
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium azide 、 双氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose
  参考文献：
  名称：

  3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?

  摘要：

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00205-0

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。
• Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor
  作者：Masamichi Tanaka、Junki Nashida、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.orglett.6b00926

  日期：2016.5.6

  in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

  在糖基受体衍生的硼酸酯存在下，使用1,2-脱水甘露糖供体和单醇受体进行β-立体选择性甘露糖基化。反应在温和条件下平稳进行，以中等至高产率提供具有高立体选择性的相应β-甘露糖苷。此外，本糖基化方法已成功地应用于阿莫莫尼脂A的全合成。
• <i>o</i>-(<i>p</i>-Methoxyphenylethynyl)phenyl Glycosides: Versatile New Glycosylation Donors for the Highly Efficient Construction of Glycosidic Linkages
  作者：Yang Hu、Ke Yu、Li-Li Shi、Lei Liu、Jing-Jing Sui、De-Yong Liu、Bin Xiong、Jian-Song Sun

  DOI：10.1021/jacs.7b07020

  日期：2017.9.13

  bestows on the new glycosyl donors enhanced stability compared to their thioglycoside counterparts toward activation conditions applied for glycosyl trichloroacetimidate (TCAI) and o-alkynylbenzoate (ABz) donor. Thus, MPEPs can also be utilized in the selective one-pot glycosylation strategy, as exemplified by the syntheses of oligosaccharides via successive glycosylations with glycosyl TCAI, ABz, and

  建立了一种使用邻（对甲氧基苯基乙炔基）苯基 (MPEP) 糖苷的新型基于炔烃活化的糖基化方案。糖基 MPEP 供体是货架稳定的，可以通过相应的邻碘苯基 ​​(IP) 糖苷通过 Sonogashira 反应有效地制备。IP 糖苷的出色稳定性及其向 MPEP 糖苷的有效转化极大地促进了 MPEP 糖基供体和 IP 糖基受体的合成。此外，他们使 MPEP 糖基化方案适用于潜在活性寡糖和糖缀合物合成策略，以 IP 糖苷为潜在形式，MPEP 糖苷为活性形式，如肺炎链球菌 3 型三糖的高效制造所示。MPEP 糖苷的酚糖苷性质赋予新的糖基供体与硫糖苷对应物相比，对应用于糖基三氯乙酰亚胺 (TCAI) 和邻炔基苯甲酸酯 (ABz) 供体的活化条件具有更高的稳定性。因此，MPEP 也可用于选择性一锅糖基化策略，例如通过连续糖基化以糖基 TCAI、ABz 和 EPMP 作为供体合成寡糖。尽管与硫糖苷供体共享相同的促进条件，但无气味的起始材料
• Stereoselective synthesis of α-linked saccharides by use of per O-benzylated 2-pyridyl 1-thio hexopyranosides as glycosyl donors and methyl iodide as an activator
  作者：Hari Babu Mereyala、G Venugopal Reddy

  DOI：10.1016/s0040-4020(01)86571-6

  日期：1991.8

  D-manno-(3) and L-rhamno-(4) configurations have been efficiently coupled with diverse sugar alcohols (6,8–11) on activation by methyl iodide to obtain the α-linked disaccharides (7,12–19). Coupling of donor 1 with the disaccharide acceptor 20 and the disaccharide donor 5 with 8 to obtain α-linked trisaccharides 21 and 22 is also described. A possible mechanism for the α-selectivity is also discussed

  描述了一种新的，实用的，立体选择性糖苷化方法，其中每个D-葡萄糖-（1），D-半乳糖-（2），D-甘露聚糖-（- ）的O-苄基化2-吡啶基1-硫代-α/β-己吡喃糖基3）和L-鼠李糖（4）构型已通过甲基碘活化与各种糖醇（6,8-11）有效偶联，获得了α-连接的二糖（7,12-19）。供体1与二糖受体20的偶联，以及二糖供体5与8的偶联，以获得α-连接的三糖21和22也进行了描述。还讨论了α选择性的可能机理。
• A mild general method for the synthesis of ∝-linked disaccharides
  作者：G.Venugopal Reddy、Vinayak R. Kulkarni、Hari Babu Mereyala

  DOI：10.1016/s0040-4039(01)80711-5

  日期：1989.1

  Stereoselective ∝-glycosylations may be achieved using stable 2-pyridyl thioglycosides (anomeric mixture) having a non-participating 2-substituent as glycosyl donor and methyl iodide as an activator.

  使用具有非参与性2-取代基作为糖基供体和甲基碘作为活化剂的稳定的2-吡啶基硫代糖苷（端基异构体混合物）可以实现立体选择性的β-糖基化。