Trimethylsilyl triflate → 2,3,4,6-tetra-O-acetyl-5-thio-glucopyranose

HRID 1297538Notes

Reaction equation

HRID 1297538 reaction equation
[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[C:13]([O:16][C@@H:17]1[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:26]([O:32][C:33](=[O:35])[CH3:34])[C@@H:25]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[S:24][CH:18]1[O:19][Si](C)(C)C)(=[O:15])[CH3:14].C(C1C=CC(CC2C=CC=CC=2C[Si](O[Si](CC2C=CC=CC=2CC2C=CC(CC)=CC=2)(C)C)(C)C)=CC=1)C>C(Cl)Cl>[C:13]([O:16][C@@H:17]1[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:26]([O:32][C:33](=[O:35])[CH3:34])[C@@H:25]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[S:24][CH:18]1[OH:19])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 694246242,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-5-thio-D-glucopyranoseHCID 694256982-(4-Ethylbenzyl)phenyltrimethylsilyl ether

Product 1

HCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranoseYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TMSOTf was added at 0° C. to a mixture of 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-5-thio-D-glucopyranose (5), 2-(4-ethylbenzyl)phenyltrimethylsilyl ether, MS4A and CH2Cl2. Instead of a product of interest (10), this reaction provided 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (7) as a by-product in a yield of 54%.

Sources & evidence

ORD record
ord-ca29c68708814ff7b5f7cb4d98352ccd
Source dataset
uspto-grants-2007_07
Patent number
US07250522B2

Reaction notes

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