Boron Trichloride → (2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triol

HRID 576425Notes

Reaction equation

HRID 576425 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C@H:19]2[C@H:24]([O:25]CC3C=CC=CC=3)[C@@H:23]([O:33]CC3C=CC=CC=3)[C@H:22]([O:41]CC3C=CC=CC=3)[C@@H:21]([CH2:49][O:50]CC3C=CC=CC=3)[S:20]2)=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1.B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C@H:19]2[C@H:24]([OH:25])[C@@H:23]([OH:33])[C@H:22]([OH:41])[C@@H:21]([CH2:49][OH:50])[S:20]2)=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 710785906-(2-Chloro-5-((2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-yl)benzyl)-2,3-dihydrobenzo[b][1,4]dioxine

Product 1

HCID 71110651(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triolYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-yl)benzyl)-2,3-dihydrobenzo[b][1,4]dioxine (126, 204 mg, 0.26 mmol) in dichloromethane (5 mL) reacted with BCl3 (1.5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 h. After quenching the reaction with methanol, solvent was evaporated under a reduced pressure. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (E047, 13 mg, 12% yield) as a white solid.

Workup

  1. customAfter quenching
  2. customthe reaction with methanol, solvent
  3. customwas evaporated under a reduced pressure
  4. customPurification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-501523608a8d4336925a0d3af374befe
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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