Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester | 182812-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 182812-51-7
• 化学式: C₃₆H₄₂N₂O₁₇S
• 分子量: 806.799
• InChiKey: JZJZRCXZTQKESM-PBFXWOOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  221.77
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium acetate 、 palladium dichloride 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 3.25h， 生成 Benzoic acid (2S,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes. II. the Synthesis of the 4- and 4′″-Monodeoxygenated Analogues

  摘要：

  Two derivatives of beta-maltosyl-(1-->4)-trehalose monodeoxygenated at positions 4 or 4''' have been synthesized in [2+2] block syntheses, After the preparation of precursors with only one free hydroxyl group the deoxy function was introduced by a Barton-McCombie reaction. Thus, glycosylation of 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside (4) with octa-O-acetyl-beta-maltose (3) gave tetrasaccharide 5 with only one free hydroxyl group at the 4-position. The 4'-position of an allyl maltoside was available selectively after removal of a 4',6'-cyclic acetal and selective benzoylation of the 6'-position. Reduction of this derivative 11 afforded allyl O-(2,3-di-O-acetyl-6-O-benzoyl-4-deoxy-alpha-D-glucopyranosyl)- (1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside (14), which was deallylated, activated as an trichloroacetimidate, and coupled to 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (20). Several compounds were fully characterized by H-1 NMR spectroscopy. Deprotection furnished the monodeoxygenated tetrasaccharides 9 and 23.

  DOI：

  10.1080/07328309608005691
• 作为产物：
  描述：

  Allyl 2,3,6,2',3'-Penta-O-acetyl-β-maltoside 在 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 3.5h， 生成 Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-3-yloxy)-3-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes. II. the Synthesis of the 4- and 4′″-Monodeoxygenated Analogues

  摘要：

  Two derivatives of beta-maltosyl-(1-->4)-trehalose monodeoxygenated at positions 4 or 4''' have been synthesized in [2+2] block syntheses, After the preparation of precursors with only one free hydroxyl group the deoxy function was introduced by a Barton-McCombie reaction. Thus, glycosylation of 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside (4) with octa-O-acetyl-beta-maltose (3) gave tetrasaccharide 5 with only one free hydroxyl group at the 4-position. The 4'-position of an allyl maltoside was available selectively after removal of a 4',6'-cyclic acetal and selective benzoylation of the 6'-position. Reduction of this derivative 11 afforded allyl O-(2,3-di-O-acetyl-6-O-benzoyl-4-deoxy-alpha-D-glucopyranosyl)- (1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside (14), which was deallylated, activated as an trichloroacetimidate, and coupled to 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (20). Several compounds were fully characterized by H-1 NMR spectroscopy. Deprotection furnished the monodeoxygenated tetrasaccharides 9 and 23.

  DOI：

  10.1080/07328309608005691