m-Chloroperbenzoic acid → 5-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenol

HRID 1713608Notes

Reaction equation

HRID 1713608 reaction equation
[Cl:1][C:2]1[C:3]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([CH2:59][CH3:60])=[CH:55][CH:54]=2)=[CH:4][C:5]([C@@:9]2([CH2:48][C:49]([CH3:51])=[CH2:50])[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:10]2)=[C:6]([OH:8])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:66]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([CH2:59][CH3:60])=[CH:55][CH:54]=2)=[CH:4][C:5]([C@:9]2([CH2:48][C:49]3([CH3:51])[CH2:50][O:66]3)[C@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[O:10]2)=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 687926765-chloro-4-(4-ethylbenzyl)-2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(2-methylallyl)tetrahydro-2H-pyran-2-yl)phenol

Product 1

HCID 866218495-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenolYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 25 (52 mg, 63 μmol) in anhydrous DCM (1 mL) was added 3-chlorobenzoperoxoic acid (21 mg, 95 μmol, 1.2 equiv). The reaction was stirred overnight, directly loaded onto a preparatory TLC plate, and eluted with 15% EtOAc in petroleum ether to give 50 (41 mg, 77% yield). LC/MS m/z 862 (M+Na).

Workup

  1. washeluted with 15% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-c96feda6099445988437514452871d1a
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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