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Au(I)催化的糖苷化反应给体

  • 关键字: Au(I)催化的糖苷化反应给体 发布者:宣传部 发布时间:2012-12-11 09:12:41 点击数: 12618次

Au(I)催化的糖苷化反应给体
(Ortho-alkynyl-benzoates glycosyl donors, for glycosylation under the catalysis of gold(I) complex)

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1. General information of the glycosyl donors

The ortho-alkynylbenzoates are a new type of glycosyl donors (Fig. 1), which undergo glycolsylation in the presence of a catalytic amount of a gold(I) complex. The carbohydrates for glycolsylation can be D-glucopyranose, D-glucosaminepyranose, D-galactopyranose, L-rhamnopyranose, L-arabofuranose, D-ribofuranose, etc. Other carbohydrate ortho-alkynylbenzoate donors can also be prepared according to the carbohydrate chemists’ needs through the same synthetic method.
 
Fig.1

Depending on the type of carbohydrates and the preparative conditions as well, a varied α:β anomer ratios of the donors are attained. Experiments showed little difference between the pair of anomers in glycosylation in accord with the glycosylation mechanism; thus the anomeric mixtures need not to be separated but can be directly used in the glycosylation reactions. For details of the methodology, see the followed references.
Ref: 1. Biao Yu, etc. Angew. Chem. Int. Ed. 2011, 50, 4933 –4936.
2. Biao Yu, etc. Angew. Chem. Int. Ed. 2011, 50, 8329 –8332.
3. Biao Yu, etc. Chem. Commun., 2010, 46, 6060–6062.
4. Biao Yu, etc. Chem. Commun., 2011, 47, 7515–7517.
5. Biao Yu, etc. Chem. Eur. J. 2010, 16, 1871 – 1882.
6. Biao Yu, etc. J. Org. Chem. 2010, 75, 6879–6888.
7. Biao Yu, etc. Tetrahedron Letters. 49 (2008) 3604–3608.

2. The catalyst and donor list

Chemical name

PPh3AuNTf2

Product code

 

CAS No.

1246810-76-3

PPh3AuNTf2

Formula

 

FW

 

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

 2,3,4,6-Tetra-O-benzoyl-D-glucopyranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1221151-98-9

Formula

C47H40O11

FW

780.8

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

 2,3,4,6-Tetra-O-benzoyl-D-glucopyranosyl ortho-cyclopropylethynybenzoate

Product code

 

CAS No.

 

Formula

C46H36O11

FW

764.8

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

 2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1038411-45-8

Formula

C47H48O7

FW

724.9

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

 3,4,6-Tri-O-acetyl-2-desoxy-2-N-phthaloyl-D-glucosaminepyranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1038411-38-9

Formula

C33H33NO11

FW

619.6

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

2,3,4-Tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1219934-70-9

Formula

C27H32O11

FW

532.53

Physical state

 

mp (°C)

 

References

 

 

 

 

 

Chemical name

2,3,4,6-Tetra-O-acetyl-D-galacopyranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1311109-71-3

Formula

 

FW

 

Physical state

 

mp (°C)

 

References

 

 

 

 

 

 

Chemical name

2,3,5-Tri-O-acetyl-L-arabofuranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1311109-69-9

Formula

 

FW

 

Physical state

 

mp (°C)

 

References

 

 

 

 

 

 

Chemical name

2,3,5-Tri-O-acetyl-D-ribofuranosyl ortho-hexynylbenzoate

Product code

 

CAS No.

1311109-67-7

Formula

 

FW

 

Physical state

 

mp (°C)

 

References