80040-79-5 (三-O-苄基-D-半乳醛,3,4,6-Tri-O-benzyl-D-galactal)

_100%

反应条件：

1.1 Reagents: Sodium hydride

参考文献：

Glycal-mediated synthesis of enantiomerically pure 5-substituted isoxazoles containing a differentially O-benzylated glycerol moiety

Weinig, Hans-Georg; Passacantilli, Pietro; Colapietro, Marcello; Piancatelli, Giovanni, Tetrahedron Letters, 2002, 43(26), 4613-4615

合成路线：1 步

_98%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 30 min, 0 °C → rt

参考文献：

Glycomimetic Ligands for the Human Asialoglycoprotein Receptor

Mamidyala, Sreeman K.; Dutta, Sanjay; Chrunyk, Boris A.; Preville, Cathy; Wang, Hong; et al, Journal of the American Chemical Society, 2012, 134(4), 1978-1981

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 15 min, 0 °C
1.2 16 h, rt
1.3 Reagents: Methanol ; rt

参考文献：

C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups

de Kleijne, Frank F. J.; Moons, Sam J.; White, Paul B.; Boltje, Thomas J., Organic & Biomolecular Chemistry, 2020, 18(6), 1165-1184

合成路线：1 步

_93%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 45 min, rt; rt → 0 °C
1.2 0 °C; 12 h, rt; rt → 0 °C
1.3 Reagents: Methanol ; 0 °C

参考文献：

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Keith, D. Jamin; Townsend, Steven D., Journal of the American Chemical Society, 2019, 141(32), 12939-12945

合成路线：1 步

_92%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 30 min, rt; 0 °C
1.2 5 min, 0 °C; 10 min, 0 °C; overnight
1.3 Reagents: Methanol ; rt

参考文献：

A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

Jiang, Fu-xiang; Liu, Qiao-zhen; Zhao, Dan; Luo, Cui-ting; Guo, Cui-ping; et al, European Journal of Medicinal Chemistry, 2014, 77, 211-222

合成路线：1 步

_92%

反应条件：

1.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium iodide Solvents: Tetrahydrofuran ; 3 h, rt

参考文献：

Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst

Madhusudan, Soni Kamlesh; Agnihotri, Geetanjali; Negi, Devendra S.; Misra, Anup Kumar, Carbohydrate Research, 2005, 340(7), 1373-1377

合成路线：1 步

_90%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C
1.2 -

参考文献：

Immunomodulatory α-galactoglycosphingolipids: Synthesis of 2'-fluoro-2'-deoxy-α-galactosylceramide and an evaluation of its immunostimulating properties

Barbieri, Lucia; Costantino, Valeria; Fattorusso, Ernesto; Mangoni, Alfonso; Basilico, Nicoletta; et al, European Journal of Organic Chemistry, 2005, (15), 3279-3285

合成路线：1 步

_90%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide , Tetrahydrofuran ; 0 °C; 4 h, 60 °C; cooled
1.2 Reagents: Carbon dioxide Solvents: Diethyl ether , Water ; neutralized, rt

参考文献：

Stereoselective Michael-type addition of organocopper reagents to enones derived from glycals in the synthesis of 2-phosphono-α-C-glycosides

Leonelli, Francesca; Capuzzi, Marinella; Calcagno, Vincenzo; Passacantilli, Pietro; Piancatelli, Giovanni, European Journal of Organic Chemistry, 2005, (13), 2671-2676

合成路线：1 步

_90%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C
1.2 0 °C; 12 h, rt

参考文献：

Immunomodulatory α-galactoglycosphingolipids: Synthesis of a 2'-O-methyl-α-gal-GSL and evaluation of its immunostimulating capacity

Barbieri, Lucia; Costantino, Valeria; Fattorusso, Ernesto; Mangoni, Alfonso; Aru, Elisabetta; et al, European Journal of Organic Chemistry, 2004, (3), 468-473

合成路线：1 步

_89%

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 3 h, 0 °C
1.2 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 20 min, 0 °C
1.3 0 °C; 12 h, 0 °C
1.4 Reagents: Ammonium chloride Solvents: Water

参考文献：

Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis

Wang, Bang; Xiong, De-Cai; Ye, Xin-Shan, Organic Letters, 2015, 17(22), 5698-5701

合成路线：1 步

878799-72-5

_89%

反应条件：

1.1 Reagents: Sodium acetate Solvents: Tetrahydrofuran ; rt → 0 °C
1.2 Reagents: Copper , Zinc ; 4.5 h, 0 °C → 10 °C

参考文献：

General Method for Synthesizing Pyranoid Glycals. A New Route to Allal and Gulal Derivatives

Boutureira, Omar; Rodriguez, Miguel Angel; Matheu, M. Isabel; Diaz, Yolanda; Castillon, Sergio, Organic Letters, 2006, 8(4), 673-675

合成路线：1 步

_87%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 30 min, 0 °C
1.2 16 h, rt
1.3 Reagents: Methanol ; rt

参考文献：

α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Moons, Sam J.; Mensink, Rens A.; Bruekers, Jeroen P. J.; Vercammen, Maurits L. A.; Jansen, Laura M.; et al, Journal of Organic Chemistry, 2019, 84(7), 4486-4500

合成路线：1 步

_86%

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 1 h, 0 °C → rt
1.2 Reagents: Sodium hydride Solvents: Dimethylformamide ; 30 min, 0 °C; 30 min, 0 °C
1.3 0 °C; overnight, rt
1.4 Reagents: Water

参考文献：

Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates

Lucchetti, Nicola ; Gilmour, Ryan, Chemistry - A European Journal, 2018, 24(61), 16266-16270

合成路线：1 步

_85%

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 2 h, rt
1.2 Reagents: Carbon dioxide ; neutralized, rt
1.3 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 16 h, 0 °C → rt

参考文献：

α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

Pilgrim, Wayne; Murphy, Paul V., Organic Letters, 2009, 11(4), 939-942

合成路线：1 步

_83%

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ; 1 d, rt
1.2 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ; 6 d, rt
1.3 Reagents: Water ; rt

参考文献：

Bronsted acid-catalyzed ring-opening polycondensation of galactose-based cyclic sulfite

Miyazaki, Ryo; Suzuki, Misaki; Shetty, Sangeetha Srinivasa; Shimazaki, Taichi; Osaka, Issey; et al, Polymer Journal (Tokyo, 2023, 55(3), 213-221

合成路线：1 步

_81%

反应条件：

1.1 Catalysts: Potassium carbonate Solvents: Methanol ; 3 h, rt
1.2 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 10 min, 0 °C
1.3 0 °C → rt; 10 h, rt
1.4 Solvents: Methanol ; 10 min, rt

参考文献：

Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogs

Shu, Penghua; Zeng, Jing; Tao, Jinyi; Zhao, Yueqi; Yao, Guangmin; et al, Green Chemistry, 2015, 17(4), 2545-2551

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 4 h, 0 °C
1.2 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 30 min, 0 °C
1.3 0 °C; 12 h, 0 °C
1.4 Reagents: Ammonium chloride Solvents: Water

参考文献：

Rhodium-Catalyzed Denitrogenative Trans-annulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides

Bi, Jingjing; Tan, Qiang; Wu, Hao; Liu, Qingfeng; Zhang, Guisheng, Organic Letters, 2021, 23(16), 6357-6361

合成路线：1 步

_79%

反应条件：

1.1 Reagents: Sodium methoxide ; 0 °C; 1 h, rt
1.2 Reagents: Amberlite IR 120 ; neutralized
1.3 Reagents: Sodium hydride Solvents: Dimethylformamide ; 40 min, 0 °C
1.4 0 °C → rt; 16 h, rt
1.5 Reagents: Methanol ; 15 min

参考文献：

Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing

Durantie, Estelle; Bucher, Christoph; Gilmour, Ryan, Chemistry - A European Journal, 2012, 18(26), 8208-8215

合成路线：1 步

_73%