Water → HCID 57684691, compound

HRID 2038494Notes

Reaction equation

HRID 2038494 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:61]=[CH:60][C:10]([CH2:11][C:12]2[CH:13]=[C:14]([C@@:19]3(OC)[C@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:23]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@H:22]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[O:20]3)[CH:15]=[CH:16][C:17]=2[Cl:18])=[CH:9][CH:8]=1)[CH:2]=[CH2:3].C([SiH](CC)CC)C.B(F)(F)F.O>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C:12]2[CH:13]=[C:14]([C@H:19]3[C@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:23]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C@H:22]([O:41][CH2:42][C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[O:20]3)[CH:15]=[CH:16][C:17]=2[Cl:18])=[CH:60][CH:61]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 57684696HCID 57684696, compound

Product 1

HCID 57684691HCID 57684691, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,3R,4S,5R,6R)-2-(3-(4-(2-(allyloxy)ethyl)benzyl)-4-chlorophenyl)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2H-pyran (intermediate BJ) (55 mg, 0.065 mmol) was taken up in 1 mL anhydrous DCM kept under argon, and triethylsilane (31.4 μL, 0.197 mmol) was added. The mixture was brought to −20° C. and borontrifluoride diethyletherate (20.1 μL, 0.164 mmol) was added. The mixture was allowed to warm and stirred at −5° C. to 0° C. for 3 h. Water (0.5 mL) was added to quench the reaction and the organic layer was separated. The aqueous layer was extracted with DCM (1 mL), and the combined organic solution was washed with brine (1 mL), dried (Na2SO4), filtered and evaporated. Preparative TLC using 10:1 hexane:EtOAc gave intermediate BK (39.5 mg, yield 60%). 1H NMR (300 MHz, CDCl3): δ 7.30-7.03 (m, 27H), 5.90 (m, 1H), 5.22 (m, 2H), 4.88-4.70 (m, 3H), 4.65-4.38 (m, 5H), 4.16-4.08 (m, 3H), 4.05-3.88 (m, 4H), 3.82-3.72 (m, 5H), 3.60-3.52 (m, 3H); LC-ESI-MS (m/z): 808 (M+H).

Workup

  1. customwas brought to −20° C.
  2. temperatureto warm
  3. customto quench
  4. customthe reaction
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with DCM (1 mL)
  7. washthe combined organic solution was washed with brine (1 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customEtOAc gave intermediate BK (39.5 mg, yield 60%)

Sources & evidence

ORD record
ord-763df62724824bddb7e38f9c515351b3
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

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