Acetic acid (4aR,6R,7R,8S,8aR)-7-acetoxy-6-((2S,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-iodomethyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester | 180588-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (4aR,6R,7R,8S,8aR)-7-acetoxy-6-((2S,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-iodomethyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS: 180588-88-9
• 化学式: C₂₆H₃₇IO₁₄
• 分子量: 700.476
• InChiKey: KUTJYNOLFAYLEV-YRJWMJGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (4aR,6R,7R,8S,8aR)-7-acetoxy-6-((2S,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-iodomethyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 在 sodium acetate 、 palladium dichloride 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-5-((2R,3R,4S,5R,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-6-iodomethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes

  摘要：

  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.

  DOI：

  10.1080/07328309608005672
• 作为产物：
  描述：

  allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 吡啶 、 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.83h， 生成 Acetic acid (4aR,6R,7R,8S,8aR)-7-acetoxy-6-((2S,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-iodomethyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes

  摘要：

  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.

  DOI：

  10.1080/07328309608005672