allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside | 97777-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: Allyl 4',6'-O-isopropylidene-β-maltoside
• CAS: 97777-14-5
• 化学式: C₁₈H₃₀O₁₁
• 分子量: 422.43
• InChiKey: ZZYBARQCDLPUNI-JBZVTRTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  156.53
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 吡啶 、 氯化亚砜 、 四丁基溴化铵 、 sodium acetate 、 sodium hydride 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三丁基氧化锡 、 palladium dichloride 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 37.5h， 生成 O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  全合成环麦芽六糖

  摘要：

  摘要首次描述了从麦芽糖开始的21步总产率为0.3％的全环麦芽索糖的全合成。麦芽糖被转化为烯丙基O-（2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷（5）和O-（4-O-乙酰基-2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-2,3,6-三-O-苄基- β-d-吡喃葡萄糖基氟（6）。化合物5与化合物6的糖基化以及产物的部分脱保护得到烯丙基O-（2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-双[O-（2 ，（3,6-三-O-苄基-gad-吡喃葡萄糖基）-（1→4）]-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷，进一步被糖基糖基化供体6，并转化为关键中间体O-（2,3,6，-三-O-苄基-α-d-吡喃吡喃糖基）-（1→4）-四[[O-（2,3,6，-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）]-2

  DOI：

  10.1016/0008-6215(87)80136-2
• 作为产物：
  描述：

  prop-2-en-1-yl-2,3,6-tri-O-acetyl-4-O-(α-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-β D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  全合成环麦芽六糖

  摘要：

  摘要首次描述了从麦芽糖开始的21步总产率为0.3％的全环麦芽索糖的全合成。麦芽糖被转化为烯丙基O-（2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷（5）和O-（4-O-乙酰基-2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-2,3,6-三-O-苄基- β-d-吡喃葡萄糖基氟（6）。化合物5与化合物6的糖基化以及产物的部分脱保护得到烯丙基O-（2,3,6-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）-双[O-（2 ，（3,6-三-O-苄基-gad-吡喃葡萄糖基）-（1→4）]-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷，进一步被糖基糖基化供体6，并转化为关键中间体O-（2,3,6，-三-O-苄基-α-d-吡喃吡喃糖基）-（1→4）-四[[O-（2,3,6，-三-O-苄基-α-d-吡喃葡萄糖基）-（1→4）]-2

  DOI：

  10.1016/0008-6215(87)80136-2

文献信息

• Preparation of 4,6-cyclo-4,6-dideoxy-hexopyranoses by palladium-mediated intramolecular cyclodehalogenation
  作者：Hans Peter Wessel、Marie-Claude Viaud、Vincent Gardon

  DOI：10.1016/0008-6215(93)80074-o

  日期：1993.7

  4,6-Cyclo-4,6-dideoxy-hexopyranoses were obtained by palladium-mediated intramolecular cyclodehalogenation. Thus, methyl 2,3-di-O-acetyl-4,6-dideoXY-4,6-diiodo-beta-D-galactopyranoside (3) afforded methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-beta-D-galactopyranoside (5) in 56% yield upon treatment with hydrogen in the presence of palladium-on-charcoal and diethylamine. The structure of 5 was proven by MS, NMR including NOE measurements, and by independent conversion of 4 to 5 by zinc-mediated Wurtz synthesis. Similarly, methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranoside (6) and O-(2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranosyl)-(l --> 4)-1,2,3,6-tetra-0-acetyl-beta-D-glucopyranose (17) were obtained along with the respective 4,6-dideoxy analogues. Also methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-beta-D-glucopyranoside (19) gave galacto-configured 5 stereoselectively.
• Total synthesis of α-cyclodextrin
  作者：Tomoya Ogawa、Yukio Takahashi

  DOI：10.1016/0008-6215(85)85239-3

  日期：1985.4
• Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes
  作者：Hans Peter Wessel、Michel Trumtel、Rudolf Minder

  DOI：10.1080/07328309608005672

  日期：1996.7

  The four derivatives of beta-maltosyl-(1 --> 4)-trehalose have been synthesized, which are monodeoxygenated at the site of one of the primary hydroxyl groups. The tetrasaccharides were constructed in [2+2] block syntheses. Thus, 6'''-deoxy-beta-maltosyl-(1 --> 4)-trehalose was prepared by selective iodination of allyl 2,3,6,2',3'-penta-O-acetyl-beta-maltoside (3) followed by catalytic hydrogenolysis and coupling with 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (9), and 6 ''-deoxy-beta-maltosyl-(1 --> 4)-trehalose by selective iodination of allyl 4',6'-O-isopropylidene-beta-maltoside (14), coupling with 9, and one-step hydrogenolysis at the tetrasaccharide level. For the synthesis of 6'-deoxy-beta-maltosyl-(1 --> 4)-trehalose, the diol 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3'-di-O-benzyl-alpha-D-glucopyranoside (22) was selectively iodinated and glycosylated with acetobromomaltose followed by catalytic hydrogenolysis. The 6-deoxy-beta-maltosyl-(1 --> 4)-trehalose was obtained upon selective iodination of a tetrasaccharide diol.