Heptane → HCID 58786124, compound
Reaction equation
CCCCCCC.B(Br)(Br)Br.C([O:19][C@@H:20]1[C@@H:25]([O:26]CC2C=CC=CC=2)[C@H:24]([O:34]CC2C=CC=CC=2)[C@@H:23]([CH2:42][O:43]CC2C=CC=CC=2)[O:22][C@H:21]1[C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][C:58]2[C:67]3[C:61]([CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[C:60]([CH3:68])[CH:59]=2)[CH:52]=1)C1C=CC=CC=1.C(Cl)Cl.C1(C)C=CC=CC=1>C(Cl)Cl.CO>[CH3:68][C:60]1[CH:59]=[C:58]([CH2:57][C:53]2[CH:52]=[C:51]([C@@H:21]3[O:22][C@H:23]([CH2:42][OH:43])[C@@H:24]([OH:34])[C@H:25]([OH:26])[C@H:20]3[OH:19])[CH:56]=[CH:55][CH:54]=2)[C:67]2[C:61]=1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2Participants
Procedure
A 1 M n-heptane solution of boron tribromide (20 ml) was added dropwise to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-[(3-methylazulen-1-yl)methyl]phenyl]-D-glucitol (0.76 g) in methylene chloride (20 ml) at −78° C. and the mixture was stirred for 30 minutes. Methylene chloride-toluene (ratio: 2:1, 60 ml) was added to the reaction mixture and methanol (6 ml) was further added to the mixture. The reaction mixture was cooled to room temperature and concentrated to the half amount, followed by adding methanol (25 ml) to the mixture and concentrating. This operation was repeated three times. The residue prepared by the concentration was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[3-[(3-methylazulen-1-yl)methyl]phenyl]-D-glucitol (0.068 g).
Workup
- additionwas further added to the mixture
- concentrationconcentrated to the half amount
- additionby adding methanol (25 ml) to the mixture
- concentrationconcentrating
- customThe residue prepared by the concentration
- customwas purified by silica gel column chromatography (chloroform-methanol)
Sources & evidence
- ORD record
- ord-0192b466887c4bd882b2214da1ebae4c
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169761B2
Reaction notes
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