Methyl triflate → HCID 23396146, compound

HRID 967348Notes

Reaction equation

HRID 967348 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([O:22][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:8][C@H:5]1SC)=[N+:2]=[N-:3].[CH2:56]1[O:66][C:65]2[CH:64]=[CH:63][C:60]([CH2:61][OH:62])=[CH:59][C:58]=2[O:57]1.COS(C(F)(F)F)(=O)=O>ClCCCl>[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([O:22][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:8][CH:5]1[O:62][CH2:61][C:60]1[CH:63]=[CH:64][C:65]2[O:66][CH2:56][O:57][C:58]=2[CH:59]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 10322Piperonyl alcoholHCID 23396150HCID 23396150, compound

Product 1

HCID 23396146HCID 23396146, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (200 mg, 0.26 mmol), 3,4-methylenedioxybenzyl alcohol 59 mg, 0.39 mmol), molecular sieves 4A (1 g) and methyltriflate (106 mg, 0.65 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature overnight. The reaction mixture was neutralized with TEA (0.5 mL) and evaporated. The residue was purified by chromatography using EtOAc—hexane 15:85 as the mobile phase to give 3,4-methylenedioxybenzyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-α,β-D-glucopyranoside (43) (173 mg, 76%).

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-8b702dbc9b914ae0b9a08752566e3488
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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