2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-4)-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside | 216572-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-4)-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
• CAS: 216572-26-8
• 化学式: C₆₆H₈₀O₂₆
• 分子量: 1289.35
• InChiKey: BFMLIXYKVLBTOS-LFZJQSPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  92.0
• 可旋转键数：
  27.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  305.86
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-4)-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 在 10% palladium on active carbon 甲醇 、 氢气 、 sodium 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、110.0 kPa 条件下， 反应 2.0h， 生成 α-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-4)-6-deoxy-α-D-glucopyranosyl 6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  The Synthesis of Four Dideoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose

  摘要：

  Four derivatives of beta-maltosyl-(1 -->4)-trehalose were prepared, each with two deoxy functions in one of the constitutive disaccharide building blocks. 2,3-Di-O-acetyl-4,6-dideoxy-4,6-diiodo-alpha-D-galactopyranosyl-(1-->4) -1,2,3,6-tetra-O-acetyl-D-glucopyranose (3) was employed as a precursor for the 4'",6'" -dideoxygenated tetrasaccharide 9: coupling of 3 with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzylidene-alpha-D-glucopyranoside (4) furnished the tetrasaccharide 5 which was deiodinated and deprotected to yield the target tetrasaccharide 9. Secondly, the dideoxygenated maltose derivative 3-deoxy-4,6-O-isopropylidene-2-O-pivaloyl-alpha-D-glucopyranosyl-(1-->4)-1,6- anhydro-3-deoxy-2-O-pivaloyl-beta-D-glucopyranose (10) was ring-opened to the anomeric acetate 11. A [2+2] block synthesis with 4 in TMS triflate mediated glycosylation gave a tetrasaccharide which was deprotected to the 3 ",3'"- dideoxygenated analogue of beta-maltosyl-(1 -->4)-trehalose. For the third tetrasaccharide, 2,3,2',3'-tetra-O-benzyl-alpha,alpha-trehalose was iodinated at the primary positions and deiodinated in the presence of palladium-on-carbon, then this acceptor was selectively glycosylated with hepta-O-acetyl-maltosyl bromide (20). Removal of protective groups furnished the maltosyl trehalose tetrasaccharide deoxygenated at positions C-6 and C-6'. To prepare a 3,3'-dideoxygenated trehalose, the free hydroxyl groups of 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopyranosyl 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopryanoside (25) were reduced by Barton-McCombie deoxygenation. One of the benzylidene groups was opened reductively with sodium cyanoborohydride. The resulting free hydroxyl group at the 4'-position was glycosylated in a Koenigs-Knorr reaction with 20 to yield the 3,3'-dideoxygenated tetrasaccharide 32, the fourth target oligosaccharide, after deprotection.

  DOI：

  10.1080/07328309808001900
• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 、 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1-4)-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  The Synthesis of Four Dideoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose

  摘要：

  Four derivatives of beta-maltosyl-(1 -->4)-trehalose were prepared, each with two deoxy functions in one of the constitutive disaccharide building blocks. 2,3-Di-O-acetyl-4,6-dideoxy-4,6-diiodo-alpha-D-galactopyranosyl-(1-->4) -1,2,3,6-tetra-O-acetyl-D-glucopyranose (3) was employed as a precursor for the 4'",6'" -dideoxygenated tetrasaccharide 9: coupling of 3 with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzylidene-alpha-D-glucopyranoside (4) furnished the tetrasaccharide 5 which was deiodinated and deprotected to yield the target tetrasaccharide 9. Secondly, the dideoxygenated maltose derivative 3-deoxy-4,6-O-isopropylidene-2-O-pivaloyl-alpha-D-glucopyranosyl-(1-->4)-1,6- anhydro-3-deoxy-2-O-pivaloyl-beta-D-glucopyranose (10) was ring-opened to the anomeric acetate 11. A [2+2] block synthesis with 4 in TMS triflate mediated glycosylation gave a tetrasaccharide which was deprotected to the 3 ",3'"- dideoxygenated analogue of beta-maltosyl-(1 -->4)-trehalose. For the third tetrasaccharide, 2,3,2',3'-tetra-O-benzyl-alpha,alpha-trehalose was iodinated at the primary positions and deiodinated in the presence of palladium-on-carbon, then this acceptor was selectively glycosylated with hepta-O-acetyl-maltosyl bromide (20). Removal of protective groups furnished the maltosyl trehalose tetrasaccharide deoxygenated at positions C-6 and C-6'. To prepare a 3,3'-dideoxygenated trehalose, the free hydroxyl groups of 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopyranosyl 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopryanoside (25) were reduced by Barton-McCombie deoxygenation. One of the benzylidene groups was opened reductively with sodium cyanoborohydride. The resulting free hydroxyl group at the 4'-position was glycosylated in a Koenigs-Knorr reaction with 20 to yield the 3,3'-dideoxygenated tetrasaccharide 32, the fourth target oligosaccharide, after deprotection.

  DOI：

  10.1080/07328309808001900