Tetrahydrofuran → HCID 69381461, compound

HRID 1375966Notes

Reaction equation

HRID 1375966 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].BrC1C=C(C=CC=1)C[C:11]1[CH:20]=[C:19]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]2)[C:12]=1[CH3:21].[CH2:25]([O:32][C@@H:33]1[C@@H:39]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:38]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:37]([CH2:56][O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:36][C:34]1=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+].[CH2:67]1[CH2:71]OC[CH2:68]1>CCCCCC>[CH2:25]([O:32][C@@H:33]1[C@@H:39]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:38]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C@@H:37]([CH2:56][O:57][CH2:58][C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[O:36][C:34]1([C:1]1[CH:71]=[CH:67][CH:68]=[C:3]([CH2:4][C:20]2[C:19]3[C:13]([CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:12]([CH3:21])[CH:11]=2)[CH:2]=1)[OH:35])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 23080562HCID 23080562, compoundHCID 178418339Butyllithium

Product 1

HCID 69381461HCID 69381461, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 1.6 M hexane solution of n-butyl lithium (2.44 ml) was added dropwise to a solution of 2-(3-bromobenzyl)-1-methylazulene (1.2 g) in THF (8.0 ml) at −78° C. and the mixture was stirred for one hour. Then, a solution of 2,3,4,6-tetra-O-benzyl-D-(+)-glucono-1,5-lactone (2.08 g) in THF (8.0 ml) was added dropwise to the reaction mixture and the mixture was stirred for one hour. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 2,3,4,6-tetra-O-benzyl-1-C-[3-[(3-methylazulen-1-yl)methyl]phenyl]-D-glucopyranose (1.74 g).

Workup

  1. stirringthe mixture was stirred for one hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bcb3083c66924054a57e275fe09ac5cf
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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