Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Methods
3.2. General Procedure for the Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates
3.3. Scaled-Up Synthesis of Compound 3
3.4. Scaled-Up Synthesis of Compound 24
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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- Anomeric H shift for β-configuration is located at δ = 5.93 and anomeric H shift for α-configuration is located at δ = 6.57 according to known data.
- Anomeric C shift for β-configuration is located at δ = 92.3 according to known data.
Sample Availability: Samples of the compounds are available from the authors. |
Entry | Base | H2O | 3 b | 4 b |
---|---|---|---|---|
1 | K2CO3 | 5 mL (278 mmol) c | 35% | 55% |
2 | K2CO3 | 2.5 mL (139 mmol) | 54% | 35% |
3 | K2CO3 | 0.5 mL (27.8 mmol) | 78% | 12% |
4 | K2CO3 | - | 88% | 4% |
5 | K2CO3 | - d | 94% | trace |
6 | Na2CO3 | - d | 80% | trace |
7 | NaHCO3 | - d | 69% | trace |
8 | Cs2CO3 | - d | 90% | trace |
9 | NaOH | - d | NR | trace |
10 | Et3N | - d | NR | trace |
Entry | PTC | Solvent | 3 b |
---|---|---|---|
1 | TBAB | DCM | 99% |
2 | TEAB | DCM | 99% |
3 | BEAC | DCM | 96% |
4 | CMAB | DCM | 97% |
5 | - | DCM | NR |
6 | TEAB | THF | <10% |
7 | TEAB | CH3CN | 78% |
8 | TEAB | DMF | <10% |
Entry | Aromatic Acids | Product | Yield b (%) |
---|---|---|---|
1 | 5 | 6 | 95 c |
2 | 7 | 8 | 98 |
3 | 9 | 10 | 91 c |
4 | 11 | 12 | 80 |
5 | 13 | 14 | 96 |
6 | 15 | 16 | 99 |
7 | 17 | 18 | 85 c |
8 | 19 | 20 | 90 |
9 | 21 | 22 | 99 c |
Entry | Aliphatic Acids | Product | Yield b (%) |
---|---|---|---|
1 | 23 | 24 | 95 c |
2 | 25 | 26 | 97 |
3 | 27 | 28 | 91 |
4 | 29 | 30 | 99 c |
5 | 31 | 32 | 72 |
6 | 33 | 34 | 92 c |
7 | 35 | 36 | 96 |
8 | 37 | 38 | 79 |
9 | 39 | 40 | 94 |
10 | 41 | 42 | 99 c |
11 | 43 | 44 | 78 |
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Chen, Y.; Lu, H.; Chen, Y.; Yu, W.; Dai, H.; Pan, X. Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates. Molecules 2017, 22, 662. https://doi.org/10.3390/molecules22040662
Chen Y, Lu H, Chen Y, Yu W, Dai H, Pan X. Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates. Molecules. 2017; 22(4):662. https://doi.org/10.3390/molecules22040662
Chicago/Turabian StyleChen, Yu, Huan Lu, Yanyu Chen, Wansheng Yu, Hui Dai, and Xianhua Pan. 2017. "Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates" Molecules 22, no. 4: 662. https://doi.org/10.3390/molecules22040662
APA StyleChen, Y., Lu, H., Chen, Y., Yu, W., Dai, H., & Pan, X. (2017). Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates. Molecules, 22(4), 662. https://doi.org/10.3390/molecules22040662