isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside | 847225-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-5-benzoyloxy-2-(hydroxymethyl)-6-propan-2-ylsulfanyl-4-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 847225-62-1
• 化学式: C₂₆H₃₀O₇S
• 分子量: 486.586
• InChiKey: LOTJONYYONFTAU-AALNHBIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside 、 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到isopropyl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Concise syntheses of arabinogalactans with β-(1→6)-linked galactopyranose backbones and α-(1→3)- and α-(1→2)-linked arabinofuranose side chains

  摘要：

  4-Methoxyphenyl glycosides of 2,3"-bis-alpha-L-arabinofuranosyl branched beta-D-(1-6)-linked galactopyranosyl tetraose (16), 3',2""-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked Plactopyranosyl hexaose (27), and a twentyose (42) consisting of beta- (1-->6)-linked D-galactopyranosyl pen tadecaoligosaccha ride backbone with alpha-L-arabinofuranosyl side chains alternatively attached at C-2 and C-3 of the middle galactose residue of each consecutive beta-(1-->6)-linked galactotriose unit of the backbone. were synthesized with isopropyl 3-O-allyl-2.4-di-O-benzoyl-1-thio-beta-D-galactopyranoside (6). 2.3.4.6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (7), 2,.3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tn-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzo-beta-D-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2.3.4-tri-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of I I with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12. and debenzoylation Rave the hexasaccharide 16 with beta-(1-->6)-linked galactopyranose backbone and 2- and 3"-linked alpha-L-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.035
• 作为产物：
  描述：

  isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 吡啶 、 sodium methylate 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 70.0h， 生成 isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Concise syntheses of arabinogalactans with β-(1→6)-linked galactopyranose backbones and α-(1→3)- and α-(1→2)-linked arabinofuranose side chains

  摘要：

  4-Methoxyphenyl glycosides of 2,3"-bis-alpha-L-arabinofuranosyl branched beta-D-(1-6)-linked galactopyranosyl tetraose (16), 3',2""-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked Plactopyranosyl hexaose (27), and a twentyose (42) consisting of beta- (1-->6)-linked D-galactopyranosyl pen tadecaoligosaccha ride backbone with alpha-L-arabinofuranosyl side chains alternatively attached at C-2 and C-3 of the middle galactose residue of each consecutive beta-(1-->6)-linked galactotriose unit of the backbone. were synthesized with isopropyl 3-O-allyl-2.4-di-O-benzoyl-1-thio-beta-D-galactopyranoside (6). 2.3.4.6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (7), 2,.3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tn-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzo-beta-D-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2.3.4-tri-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of I I with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12. and debenzoylation Rave the hexasaccharide 16 with beta-(1-->6)-linked galactopyranose backbone and 2- and 3"-linked alpha-L-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.035

文献信息

• Concise syntheses of arabinogalactans with β-(1→6)-linked galactopyranose backbones and α-(1→3)- and α-(1→2)-linked arabinofuranose side chains
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.bmc.2004.10.035

  日期：2005.2

  4-Methoxyphenyl glycosides of 2,3"-bis-alpha-L-arabinofuranosyl branched beta-D-(1-6)-linked galactopyranosyl tetraose (16), 3',2""-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked Plactopyranosyl hexaose (27), and a twentyose (42) consisting of beta- (1-->6)-linked D-galactopyranosyl pen tadecaoligosaccha ride backbone with alpha-L-arabinofuranosyl side chains alternatively attached at C-2 and C-3 of the middle galactose residue of each consecutive beta-(1-->6)-linked galactotriose unit of the backbone. were synthesized with isopropyl 3-O-allyl-2.4-di-O-benzoyl-1-thio-beta-D-galactopyranoside (6). 2.3.4.6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (7), 2,.3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tn-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzo-beta-D-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2.3.4-tri-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of I I with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12. and debenzoylation Rave the hexasaccharide 16 with beta-(1-->6)-linked galactopyranose backbone and 2- and 3"-linked alpha-L-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.