Methanol → (1R,2S,3R,6R)-6-[2-(4-Cyclopropyl-benzyl)phenoxy]-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

HRID 554564Notes

Reaction equation

HRID 554564 reaction equation
B(Cl)(Cl)Cl.[CH:5]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C@H:22]3[C@H:27]([O:28]CC4C=CC=CC=4)[C@@H:26]([O:36]CC4C=CC=CC=4)[C@H:25]([O:44]CC4C=CC=CC=4)[C:24]([CH2:52][O:53]CC4C=CC=CC=4)=[CH:23]3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1.CC1C(C)=C(C)C(C)=C(C)C=1.CO>C(Cl)Cl>[CH:5]1([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C@H:22]3[C@H:27]([OH:28])[C@@H:26]([OH:36])[C@H:25]([OH:44])[C:24]([CH2:52][OH:53])=[CH:23]3)=[CH:12][CH:13]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 12784PentamethylbenzeneHCID 25135Boron TrichlorideHCID 674611171-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene

Product 1

HCID 11625132(1R,2S,3R,6R)-6-[2-(4-Cyclopropyl-benzyl)phenoxy]-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triolYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, a boron trichloride 1.0 M methylene chloride solution (160 μL, 0.16 mmol) was added to a solution of 1-(4-cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene (12 mg, 0.016 mmol) and pentamethylbenzene (24 mg, 0.17 mmol) in methylene chloride (300 μL) at −78° C., and the mixture was stirred at the same temperature for 1.5 hours. After addition of methanol, the temperature of the resulting solution was raised to room temperature and the solvent was distilled under reduced pressure. The obtained residue was purified by preparative TLC [developing solution=methanol:methylene chloride (1:8)] to obtain the title compound (4.1 mg, 70%).

Workup

  1. distillationthe solvent was distilled under reduced pressure
  2. customThe obtained residue was purified by preparative TLC [developing solution=methanol:methylene chloride (1:8)]

Sources & evidence

ORD record
ord-1eaf7473534c44e092fd832a317b0749
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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