HCID 67115799, compound → (2S,3R,4R,5S,6R)-2-(3-chroman-6-ylmethyl-4-cyclopropyl-phenyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

HRID 72606Notes

Reaction equation

HRID 72606 reaction equation
[CH:1]1([C:4]2[CH:20]=[CH:19][C:18]([CH:21]3[C@H:26]([O:27]CC4C=CC=CC=4)[C@@H:25]([O:35]CC4C=CC=CC=4)[C@H:24]([O:43]CC4C=CC=CC=4)[C@@H:23]([CH2:51][O:52]CC4C=CC=CC=4)[O:22]3)=[CH:17][C:5]=2[CH2:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[O:13][CH2:12][CH2:11][CH2:10]3)[CH2:3][CH2:2]1>C1COCC1.[Pd]>[O:13]1[C:14]2[C:9](=[CH:8][C:7]([CH2:6][C:5]3[CH:17]=[C:18]([C@H:21]4[C@H:26]([OH:27])[C@@H:25]([OH:35])[C@H:24]([OH:43])[C@@H:23]([CH2:51][OH:52])[O:22]4)[CH:19]=[CH:20][C:4]=3[CH:1]3[CH2:2][CH2:3]3)=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 67115799HCID 67115799, compound

Product 1

HCID 52913289(2S,3R,4R,5S,6R)-2-(3-chroman-6-ylmethyl-4-cyclopropyl-phenyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triolYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-[2-cyclopropyl-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (650 mg) in THF (5 mL) was added 10% palladium charcoal activated (dry) (100 mg), methanol (5 mL), and conc. HCl (0.2 mL). The reaction mixture was stirred under hydrogen atmosphere (bladder pressure) overnight then filtered through a celite bed. The filtrate was concentrated and purified by preparative HPLC to furnish (2S,3R,4R,5S,6R)-2-(3-chroman-6-ylmethyl-4-cyclopropyl-phenyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (63 mg).

Workup

  1. dry with material(dry) (100 mg), methanol (5 mL), and conc. HCl (0.2 mL)
  2. filtrationthen filtered through a celite bed
  3. concentrationThe filtrate was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4c49d1d6ff574c37b03492a161150f4b
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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