methyl 6-deoxy-6-iodo-α-D-galactopyranoside | 35904-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-iodo-α-D-galactopyranoside
• 英文别名: methyl α-D-6-deoxy-6-iodogalactopyranoside；6-Iod-methyl-α-D-galactopyranosid；Methyl 6-deoxy-6-iodo-alpha-D-galactoside；(2S,3R,4S,5R,6S)-2-(iodomethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 35904-60-0
• 化学式: C₇H₁₃IO₅
• 分子量: 304.082
• InChiKey: MAZXJZHWRBSRKM-PZRMXXKTSA-N

物化性质

• 熔点：
  175.0-175.6 °C(Solv: methanol (67-56-1))
• 沸点：
  407.2±45.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-iodo-α-D-galactopyranoside 在 samarium diiodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 (1S,2S,3S,4S,5S)-2,3,4-tris[[tert-butyl(dimethyl)silyl]oxy]-5-methylcyclopentan-1-ol
  参考文献：
  名称：

  二碘化Sa促进的6-脱氧-6-碘正吡喃果糖类的级联反应：碳水化合物衍生物的新的环收缩。

  摘要：

  DOI：

  10.1021/jo961116+
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 咪唑 、 硫酸 、 碘 、 乙酰氯 、 三苯基膦 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 97.0h， 生成 methyl 6-deoxy-6-iodo-α-D-galactopyranoside
  参考文献：
  名称：

  An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells

  摘要：

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.014

文献信息

• Regioselective Conversion of Primary Alcohols into Iodides in Unprotected Methyl Furanosides and Pyranosides
  作者：Robert Madsen、Philip R. Skaanderup、Carina Storm Poulsen、Lene Hyldtoft、Malene R. Jørgensen

  DOI：10.1055/s-2002-33641

  日期：——

  the primary hydroxy group in methyl glycosides with iodide. The first method is a modification of a literature procedure employing triphenylphosphine and iodine, where purification has been carried out on a reverse phase column in order to efficiently separate the desired iodoglycosides from triphenylphosphine oxide. The second method employs a new procedure using sulfonylation in pyridine with sterically

  描述了用碘化物对甲基糖苷中的伯羟基进行区域选择性置换的两种方法。第一种方法是使用三苯膦和碘对文献程序的改进，其中纯化在反相柱上进行，以便有效地从三苯膦氧化物中分离出所需的碘苷。第二种方法采用了一种新的方法，即在吡啶中用空间位阻的 2,4,6-三氯和 2,4,6-三溴苯磺酰氯进行磺酰化。如此形成的磺酸盐是有效的离去基团，并且可以在一锅法中进行碘化物的取代。碘苷的保护也描述为用三氯乙酰亚胺苄酯苄基化或用三乙基甲硅烷基氯甲硅烷基化。
• Chiron approach to the total synthesis of Amaryllidaceae alkaloid (+)-lycoricidine
  作者：Puli Saidhareddy、Arun K. Shaw

  DOI：10.1016/j.tet.2017.10.033

  日期：2017.11

  A highly stereoselective total synthesis of Amaryllidaceae alkaloid starting from α-d-galactopyranoside has been described. The salient features of this total synthesis are Ferrier carbocyclization reaction for the synthesis of ring A and Suzuki Miyaura coupling of chiral α-iodo enone fragment with aromatic boronic acid followed by modified Bischler-Napieralski cyclization reaction to form the lactam

  已经描述了从α- d-吡喃半乳糖苷开始的高立体选择性全合成芳樟科生物碱。该总合成的显着特征是用于合成环A的费勒碳环化反应和手性α-碘​​烯酮片段与芳族硼酸的Suzuki Miyaura偶联，然后进行修饰的Bischler-Napieralski环化反应以形成内酰胺环。
• Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation
  作者：Mattie S.M. Timmer、Emma M. Dangerfield、Janice M.H. Cheng、Shivali A. Gulab、Bridget L. Stocker

  DOI：10.1016/j.tetlet.2011.07.044

  日期：2011.9

  A remarkably efficient synthesis of the biologically important iminosugar 1-deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate-containing piperidine skeleton over its five-membered counterpart. (C) 2011 Elsevier Ltd. All rights reserved.
• Zinc-Mediated Fragmentation of Methyl 6-Deoxy-6-iodo-hexopyranosides
  作者：Philip R. Skaanderup、Lene Hyldtoft、Robert Madsen

  DOI：10.1007/s007060200021

  日期：2002.4.1

  An improved procedure was developed for the zinc-mediated fragmentation of protected and unprotected methyl 6-deoxy-6-iodo-hexopyranosides. The method employs sonication of the iodoglycoside with zinc dust in a THF/H2O mixture.
• Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates
  作者：Juan Manuel Benito、Carmen Ortiz Mellet、José Manuel Garcı́a Fernández

  DOI：10.1016/s0008-6215(99)00273-6

  日期：1999.1

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.