13096-62-3 2,3,4,6-四苄基-D-吡喃葡萄糖酸-1,5-内酯

中文名称: 2,3,4,6-四苄基-D-吡喃葡萄糖酸-1,5-内酯
英文名称: 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone
CAS号
分子式: C₃₄H₃₄O₆
分子量: 538.63
更新日期: 2026-06-23

名称和标识

中文名: 2,3,4,6-四苄基-D-吡喃葡萄糖酸-1,5-内酯
英文名: 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone
CAS号: 13096-62-3
分子式: C34H34O6
分子量: 538.63
中文别名: 2,3,4,6-四-O-苄基-D-葡萄糖-δ-内酯; 2,3,4,6-四邻苄基-D-葡萄糖酸内酯; 2,3,4,6-四-氧-苄基-D-吡喃葡萄糖酸-1,5-内酯; D-吡喃葡萄糖酸-1,5-内酯
英文别名: 2,3,4,6-TETRAKIS-O-(PHENYLMETHYL)-D-GLUCONIC ACID LACTONE; D-Gluconic acid, 2,3,4,6-tetrakis-O-(phenylMethyl)-, δ-lactone; 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-Gluconic Acid, D-Lactone; 2,3,4,6-tetra-O-benzyl-D-glucopyranolactone; 2,3,4,6-Tetra-O-benzyl-D-gluconic acid-δ-lactone; (3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one; (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one

物化属性

LogP: 7.74
LogS: -6.26
PSA: 63.22 Å²
外观: 无色至浅黄色澄清液体
密度: 1.2±0.1 g/cm³
折射率: 1.614
沸点: 677.7±55.0 °C (760 mmHg)
闪点: 283.1±31.5 °C

生产及用途

用途与制备

5-内酯是糖类化合物，可用作医药中间体。

医药

合成路线 1（1. 合成：13096-62-3）

产率：82% 合成条件：Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.33 h; Molecular sieve Stage #2: at 20℃; for 2 h; 实验步骤：实施例XXI 2,3,4,6-四-O-苄基-D-吡喃葡萄糖酮将4g新活化的分子筛4和3.3g N-甲基吗啉-N-氧化物加入到10.0g 2,3,4的溶液中在140ml二氯甲烷中的6-四-O-苄基-α-D-吡喃葡萄糖。将溶液在环境温度下搅拌20分钟，然后加入0.3g过钌酸四丙基铵。在环境温度下搅拌2小时后，将溶液用二氯甲烷稀释并通过硅藻土过滤。滤液用硫代硫酸钠水溶液和水洗涤，然后用硫酸钠干燥。除去溶剂后，将残余物通过硅胶色谱分离（环己烷/乙酸乙酯4：1）。产量：8.2g（理论值的82％）质谱（ESI +）：m / z = 539 [M + H] + 参考文献：

[1] Patent: WO2005/92877, 2005, A1. Location in patent: Page/Page column 63 [2] Patent: US2006/189548, 2006, A1. Location in patent: Page/Page column 26-27 [3] Patent: US2006/234953, 2006, A1. Location in patent: Page/Page column 14 [4] Patent: US2007/4648, 2007, A1. Location in patent: Page/Page column 14 [5] Patent: US2007/27092, 2007, A1. Location in patent: Page/Page column 26 [6] Tetrahedron, 1994, vol. 50, # 14, p. 4215 - 4224 [7] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 8, p. 1872 - 1878

合成路线 2（2. 合成：13096-62-3）

产率：93% 合成条件：at 20℃; 实验步骤：向2,3,4,6-四-O-苄基-D-吡喃葡萄糖苷1（5g，9.25mmol）的DMSO（25mL）溶液中加入乙酸酐（15mL）。将混合物搅拌过夜，然后用水（200mL）稀释，然后用乙酸乙酯萃取5次。将合并的有机相用饱和NaCl溶液洗涤，用无水Na 2 SO 4干燥，过滤，并减压浓缩。通过柱色谱（石油醚/乙酸乙酯= 8/1）纯化残余物，得到化合物2（4.63g，93％），为无色油状物。 1H-NMR（DMSO-d-6,400MHz）：7.35-7.22（m，20H），4.86（d，11.2Hz，1H），4.71-4.59（m，5H），4.56-4.47（m，3H）， 4.37（d，6.4Hz，1H），4.02（t，6Hz，1H），3.88（t，6.8Hz，1H），3.73-3.66（m，2H）。 13 C-NMR（DMSO-d-6,100MHz）：169.06,137.85,137.81,137.60,137.49,128.23,127.86,127.79,127.74,127.71,127.65,127.57,79.59,77.56,77.37,75.28,72.71,72.36,72.28 ，68.28。 参考文献：

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 642 - 644 [2] Organic Process Research and Development, 2014, vol. 18, # 1, p. 66 - 81 [3] Patent: US2005/209166, 2005, A1. Location in patent: Page/Page column 26 [4] Patent: WO2006/138163, 2006, A2. Location in patent: Page/Page column 25-26

合成路线 3（3. 合成：13096-62-3）

产率：98% 合成条件：With acetic anhydride In dimethyl sulfoxide at 20℃; for 10 h; 实验步骤：向内酯17（37.4g，68.8mmol）在（195mL，2.75mol）DMSO中的溶液中将溶液在室温下搅拌20分钟，然后加入乙酸酐（130mL，1.37mol）。在环境温度下搅拌10小时后，通过加入冷（0℃）淬灭溶液。 H2O（500mL）加完后，将溶液逐渐升至室温。分离有机层，水层用EtOAc萃取。将合并的有机层用盐水洗涤，用无水Na 2 SO 4干燥，过滤并真空浓缩。通过硅胶柱色谱法（EtOAc-石油醚= 1:20）纯化得到的粗残余物，得到标题化合物（36.4g，98％），为无色油状物。 1H NMR（400MHz，CDCl3）δ7.40-7.17（m，20H），5.00（d，J = 11.2Hz，1H），4.76-4.45（m，8H），4.14（d，J = 6.4Hz，1H），3.98-3.90（m，2H），3.72-3.64（m，2H）。 参考文献：

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