HCID 10989032, compound → HCID 11096141, compound

HRID 1268718Notes

Reaction equation

HRID 1268718 reaction equation
CC1(C)[O:6][C@@H:5]([C@@H:7]2[C@@H:14]3[C@@H:10]([O:11][C:12]([CH3:16])([CH3:15])[O:13]3)[CH2:9][S:8]2)[CH2:4][O:3]1>CC(O)=O>[CH3:15][C:12]1([CH3:16])[O:11][C@H:10]2[CH2:9][S:8][C@H:7]([C@H:5]([OH:6])[CH2:4][OH:3])[C@H:14]2[O:13]1

Participants

3

Reactant 1

HCID 10989032HCID 10989032, compound

Product 1

HCID 11096141HCID 11096141, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 109 (5.4 g, 20.1 mmol) in 30% aqueous AcOH (150 mL) was stirred at room temperature for 50 h. The reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to give the diol 110 (3.4 g, 75%) as a syrup: 1H NMR (CDCl3) δ 1.34 (s, 3H, CH3), 1.53 (s, 3H, CH3), 2.90 (dd, 1H, J=12.9, 2.2 Hz, 6′-CHH), 3.09 (dd, 1H, J=12.9, 4.8 Hz, 6′-CHH), 3.27 (dd, 1H, J=7.8, 1.9 Hz, 4′-H), 3.49 (br s, 2H, 2×OH), 3.58–3.72 (m, 2H, HOCHHCH(OH)), 3.79 (dd, 1H, J=11.0, 2.9 Hz, HOCHH), 4.93 (m, 2H, 3a-H, 6a-H); Anal. Calcd for C19H16O4S: C, 49.07; H, 7.32; S, 14.56 . Found: C, 49.24; H, 7.72; S, 14.23.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8d69b3bfcdf9455e948ebaef5560ea09
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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