methyl 2,6-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside | 73712-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside
• 英文别名: methyl α-D-olivomycoside；methyl α-D-evermicoside；3t,4c-Dihydroxy-6t-methoxy-2r,4t-dimethyl-tetrahydropyran；(2R,3R,4R,6S)-6-methoxy-2,4-dimethyloxane-3,4-diol
• CAS: 73712-09-1
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: YLMFFJPPIFKCBQ-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside 在 2,4,6-三甲基吡啶 、 sodium periodate 、 乙酸乙烯酯 、 三乙胺 、 二异丙胺 、 甲苯 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Synthesis of the disaccharide CD fragment found in everninomicin-C and -D, avalamycin-A and -C and curamycin-A: stereochemistry at the spiro-ortholactone center

  摘要：

  DOI：

  10.1016/s0040-4039(00)95922-7
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-3-C-<(trimethylsilyl)methyl>-α-D-ribo-hexopyranoside 在 sodium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 Dowex 50W-X₈ 、 mercury(II) diacetate 、 三正丁基氢锡 、 sodium methylate 、 barium carbonate 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 28.5h， 生成 methyl 2,6-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Preparation of 3-C-methylene sugars by Peterson olefination

  摘要：

  DOI：

  10.1021/jo00139a035

文献信息

• Ammocidin, a New Apoptosis Inducer in Ras-dependent Cells from Saccharothrix sp. II. Physico-chemical Properties and Structure Elucidation.
  作者：RYO MURAKAMI、TAIJIRO TOMIKAWA、KAZUO SHIN-YA、JUNKO SHINOZAKI、TAKAYUKI KAJIURA、HARUO SETO、YOICHI HAYAKAWA

  DOI：10.7164/antibiotics.54.714

  日期：——

  The structure of ammocidin, a new apoptosis inducer in Ras-dependent cells from Saccharothnx sp. AJ9571, was elucidated to be as shown in Fig. 1 by NMR and degradation studies. Ammocidin consists of a 20-membered macrolide ring and three deoxy sugars identified as 6-deoxy-L-glucose, D-digitoxose and D-olivomycose.

  ammocidin 的结构，一种来自 Saccharothnx sp 的 Ras 依赖性细胞的新型凋亡诱导剂。通过NMR和降解研究表明AJ9571如图1所示。阿莫西丁由 20 元大环内酯环和三种脱氧糖组成，分别为 6-脱氧-L-葡萄糖、D-洋地黄糖和 D-橄榄菌糖。
• Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate
  作者：Robert M. Giuliano、Frank J. Jr. Villani

  DOI：10.1021/jo00106a035

  日期：1995.1

  The additions of organometallic reagents to two pentodialdo-1,4-furanosides (methyl 3-O-benzyl-2-deoxy-alpha-D-erythro-pentofuranoside and its beta-anomer) were carried out under a variety of experimental conditions. Methylmagnesium halides, methyllithium, methylcerium and the organotitanium reagent MeTi(OiPr)(3) were reacted with the pentodialdo-1,4-furanosides in an effort to determine if the stereoselectivity of addition to the formyl group is the result of chelation or nonchelation control and to determine the effect of anomeric configuration. The stereochemistry of the products was assigned by NMR methods and correlation with known compounds synthesized previously. The stereoselectivity of addition depends on the configuration at the anomeric center of the dialdose, with the beta-anomer giving mainly the product of a non-chelation-controlled addition and the beta-anomer giving the opposite stereoselectivity. The major product obtained from the beta-anomer was utilized as a key intermediate in the synthesis of two branched-chain carbohydrates, axenose and evermicose, found in antibiotics. Methylcerium additions are the most efficient method for introducing the branching methyl group in a 2-deoxyfuranosid-3-ulose.
• Synthesis of the disaccharide CD fragment found in everninomicin-C and -D, avalamycin-A and -C and curamycin-A: stereochemistry at the spiro-ortholactone center
  作者：Jean-Marie Beau、Guy Jaurand、Jacques Esnault、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)95922-7

  日期：1987.1
• Preparation of 3-C-methylene sugars by Peterson olefination
  作者：Francis A. Carey、Walter C. Frank

  DOI：10.1021/jo00139a035

  日期：1982.8