methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactoside | 6087-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactoside
• 英文别名: methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranoside；methyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranoside；methyl 3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranoside；2-deoxy methyl galactoside；Methyl-(tri-O-acetyl-α-D-lyxo-2-desoxy-hexopyranosid)；methyl-(tri-O-acetyl-α-D-lyxo-2-deoxy-hexopyranoside)；[(2R,3R,4R,6S)-3,4-diacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 6087-42-9
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: JTQYAWBAXLZBQR-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-taloside 在 过氧化双月桂酰 作用下， 反应 6.0h， 以93%的产率得到methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactoside
  参考文献：
  名称：

  通过无金属脱碘反应实际合成 2-脱氧糖

  摘要：

  摘要 2-脱氧糖苷，其中 C-2 羟基被氢原子取代，是许多生物活性天然产物和药物分子中的重要基序。本文报道了一种使用环己烷和乙酸乙酯作为共溶剂的改进的过氧化二月桂酰介导的自由基脱碘反应。这是一种对环境无害的方案，可在温和条件下平稳运行，并允许以高达 98% 的收率有效制备一系列 2-脱氧糖苷。

  DOI：

  10.1080/07328303.2021.2015365

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。
• A new aspect of the reactivity of sodium dithionite provides a facile route to 2-deoxy-α-glycosides
  作者：Valeria Costantino、Ernesto Fattorusso、Concetta Imperatore、Alfonso Mangoni

  DOI：10.1016/s0040-4039(02)02280-3

  日期：2002.12

  dehalogenation of protected 2-iodo-2-deoxyglycosides. Combined with the well-known iodonium-mediated haloalkoxylation, this reaction provides an easy, mild and highly stereoselective route for preparation of 2-deoxy-α-glycosides from glycals.

  已知引起α-卤代羰基化合物脱卤的连二亚硫酸钠也诱导了被保护的2-碘-2-脱氧糖苷的脱卤。结合众所周知的碘鎓介导的卤代烷氧基化反应，该反应提供了一种简单，温和且高度立体选择性的途径，用于从糖类制备2-脱氧-α-糖苷。
• Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
  作者：Ornelio Rosati、Massimo Curini、Federica Messina、Maria Carla Marcotullio、Giancarlo Cravotto

  DOI：10.1007/s10562-012-0932-z

  日期：2013.2

  conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.Graphical Abstract

  层状 α-磺基苯基膦酸锆 - 甲膦酸是一种固体酸催化剂，可在温和的反应条件下，在短时间内和良好的产率催化 d-乙二醇和醇类亲核试剂的费里尔重排。值得注意的是，α-磺基苯基膦酸锆-甲膦酸锆和溴化锂的组合改变了该过程的区域选择性，以良好的收率提供了 2-脱氧糖。
• Foster et al., Journal of the Chemical Society, 1951, p. 980,985
  作者：Foster et al.

  DOI：——

  日期：——
• The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Marlena Matuszewska、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(02)00288-4

  日期：2002.11

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.