1,6-anhydro-β-D-galactopyranose | 14059-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-β-D-galactopyranose
• 英文别名: 1,6-anhydro-β-D-talopyranose；1,6-anhydrotalopyranose；galactosan；talosan；1,6-Anhydro-beta-d-talopyranose；(1R,2R,3S,4S,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• CAS: 14059-73-5
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: TWNIBLMWSKIRAT-QBFJYBIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  1,6-anhydro-β-D-galactopyranose 生成 1,6-anhydro-2-O-benzyl-β-D-idopyranose
  参考文献：
  名称：

  CRUZADO, M. CARMEN;MARTIN-LOMAS, MANUEL, CARBOHYDR. RES., 175,(1988) N 2, 193-199

  摘要：

  DOI：
• 作为产物：
  描述：

  左旋葡萄糖酮 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 水 、 碘 、 silver(I) acetate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1,6-anhydro-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis of 1,6:3,4-Dianhydro-b-D-talopyranose from Levoglucosenone: Epoxidation of Olefin via trans-Iodoacetoxylation

  摘要：

  Levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-beta-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis.

  DOI：

  10.3987/com-92-6112

文献信息

• The regioselectivity of tributyltin ether-mediated benzylation of 1,6-anhydro-β-d-hexoipyranoses
  作者：M. Carmen Cruzado、Manuel Martin-Lomas

  DOI：10.1016/0008-6215(88)84142-9

  日期：1988.5

  Abstract The benzylation of 1,6-anhydro-β- d -galactopyranose and the manno , allo , altro , gulo , talo , gluco , and ido isomers, using bis(tributyltin) oxide and N -methylimidazole, tetrabutylammonium bromide, tetrabutylammonium iodide, or tetrabutylammonium fluoride as catalyst, has been studied. The results confirm the importance of the catalyst in the benzylation reactions and indicate that the

  摘要用双（三丁基锡）氧化物和N-甲基咪唑，四丁基溴化铵，四丁基碘化铵，1,6-脱水-β-d-吡喃半乳糖和甘露糖，同分异构体，altro，gulo，talo，葡萄糖和氨基异构体进行苄基化或以四丁基氟化铵为催化剂已被研究。结果证实了催化剂在苄基化反应中的重要性，并且表明顺式-轴向羟基的存在似乎对于区域选择性苄基化是必需的。
• The preferred rotamer about the C₅—C₆ bond of <scp>D</scp>-galactopyranoses and the stereochemistry of dehydrogenation by <scp>D</scp>-galactose oxidase
  作者：Hiroshi Ohrui、Yoshihiro Nishida、Hiroko Higuchi、Hiroshi Hori、Hiroshi Meguro

  DOI：10.1139/v87-191

  日期：1987.6.1

  ¹H nuclear magnetic resonance studies on D-galactopyranoses with chirally deuterated hydroxymethyl groups revealed that the preferred rotamer about the C₅—C₆ bond of the D-galactopyranoses was not tg but gt. Studies on the stereochemistry of dehydrogenation of D-galactose oxidase from Dactyliumdendroides with chirally pure deuterated methyl β-D-galactopyranosides showed that there were two mechanisms for the enzymatic reaction: an efficient pro-S hydrogen atom specific oxidation and a far less efficient non-specific or pro-R specific oxidation.

  使用手性氘代羟甲基基团的核磁共振技术研究D-半乳糖苷的结构，发现其C5-C6键的优先构象不是tg而是gt。使用手性纯的氘代甲基β-D-半乳糖苷研究Dactyliumdendroides的D-半乳糖氧化酶的立体化学，发现酶反应存在两种机制：高效的pro-S氢原子特异性氧化和远不如前者的非特异性或pro-R特异性氧化。
• The heterogeneous, catalytic, transfer hydrogenolysis of tri- O -benzyl derivatives of 1,6-anhydro-β- d -hexopyranoses
  作者：M. Carmen Cruzado、Manuel Martin-Lomas

  DOI：10.1016/s0008-6215(00)90910-8

  日期：1987.12
• CRUZADO, M. CARMEN;MARTIN-LOMAS, MANUEL, CARBOHYDR. RES., 175,(1988) N 2, 193-199
  作者：CRUZADO, M. CARMEN、MARTIN-LOMAS, MANUEL

  DOI：——

  日期：——
• Synthesis of 1,6:3,4-Dianhydro-b-D-talopyranose from Levoglucosenone: Epoxidation of Olefin via trans-Iodoacetoxylation
  作者：Katsuya Matsumoto、Takashi Ebata、Koshi Koseki、Koji Okano、Hiroshi Kawakami、Hajime Matsushita

  DOI：10.3987/com-92-6112

  日期：——

  Levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-beta-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis.