5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose | 62853-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose
• 英文别名: (-)-5-Deoxy-1,2-di-O-isopropylidene-3-O-methyl-D-glucofuranose；1,2-O-isopropylidene-3-O-methyl-5-deoxy-α-D-glucofuranose；2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol
• CAS: 62853-46-7
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: WGJOJZRXTABKKH-BZNPZCIMSA-N

物化性质

• 沸点：
  293.9±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 硫酸 、 乙酸酐 、 sodium hydride 、 苯基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 173.5h， 生成 (4R,5S)-5-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methoxy-butyl)-4-(2-methyl-allyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Synthetic studies on the carbomycins (magnamycins): an exception to the enantioselective synthesis of .beta.-alkyl carboxylic acids via chiral oxazolines

  摘要：

  DOI：

  10.1021/jo00332a023
• 作为产物：
  描述：

  5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-alpha-D-xylo-hex-5-enofuranose 在 sodium hydroxide 、 2-甲基-2-丁烯 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose
  参考文献：
  名称：

  Synthetic studies on the carbomycins (magnamycins): an exception to the enantioselective synthesis of .beta.-alkyl carboxylic acids via chiral oxazolines

  摘要：

  DOI：

  10.1021/jo00332a023

文献信息

• Process for deoxygenating secondary alcohols
  申请人：Schering Corporation

  公开号：US04078139A1

  公开（公告）日：1978-03-07

  The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100.degree. C and under an inert atmosphere. The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity. Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.

  将至少具有一个次级羟基且具有任何氨基保护的有机化合物中的次级羟基团从中去除的过程，包括将所述次级羟基团的反应性酯（所选自O-烷基硫酯和O-烷基硒酯组成的群）与至少一摩尔的有机锡氢化物（优选为三正丁基锡烷）在惰性、无极性溶剂中，在至少约100摄氏度的温度下，在惰性气氛下反应。该过程特别适用于去除氨基糖苷类抗生素中的次级醇，以产生具有抗菌活性的去氧衍生物。还描述了新颖的O-sec.-烷基硫代苯甲酸酯、O-sec.-烷基-S-甲基黄原酸酯、N-(sec.-烷氧硫代羰基)-咪唑酯和至少具有一个次级O-烷基基团的双O-烷基硫代碳酸酯，这些是所述过程的有用中间体。
• Total synthesis of carbomycin B and josamycin (leucomycin A3)
  作者：Kuniaki Tatsuta、Yoshiya Amemiya、Shunji Maniwa、Mitsuhiro Kinoshita

  DOI：10.1016/s0040-4039(00)78621-7

  日期：1980.1

  The stereospecific total synthesis of macrolide antibiotics, carbomycin B and josamycin (leucomycin A3), is described. The key aglycone has been synthesized by coupling two segments of C1–C10 and C11–C16 portions, which are stereospecifically derived from glucose.

  描述了大环内酯类抗生素卡波霉素B和交沙霉素（leucomycin A 3）的立体定向全合成。关键的糖苷配基是通过耦合C1–C10和C11–C16部分的两个片段而合成的，这两个片段是立体定向衍生自葡萄糖的。
• N-Phenylselenophthalimide. A useful reagent for the facile transformation of (1) carboxylic acids into either selenol esters or amides and (2) alcohols into alkyl phenyl selenides
  作者：Paul A. Grieco、John Yan Jaw、D. A. Claremon、K. C. Nicolaou

  DOI：10.1021/jo00319a037

  日期：1981.3
• Calcium hypochlorite-mediated oxidation of primary alcohols to methyl esters
  作者：Chriss E. McDonald、Lois E. Nice、Anthony W. Shaw、Nestor B. Nestor

  DOI：10.1016/s0040-4039(00)73550-7

  日期：1993.4

  Primary aliphatic alcohols can be converted to methyl esters using calcium hypochlorite as the oxidant. Primary benzyl alcohols can also be converted efficiently to methyl benzoates.
• Synthesis of 16-membered-ring macrolide antibiotics. 4. Carbomycin B and leucomycin A3: total synthesis of cyclic key intermediate
  作者：K. C. Nicolaou、M. R. Pavia、S. P. Seitz

  DOI：10.1021/ja00395a044

  日期：1981.3