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Ammonium Chloride → 1-c-[5-(Azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-o-benzyl-d-glucopyranose

HRID 1375989
Notes
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Reaction equation

HRID 1375989 reaction equation
C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:30]=[CH:29][C:17]([CH2:18][C:19]2[CH:28]=[C:27]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=[CH:26]3)[CH:20]=2)=[CH:16][C:15]=1Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:32]([O:39][C@@H:40]1[C@@H:46]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@H:45]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@@H:44]([CH2:63][O:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[O:43][C:41]1=[O:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH:20]1[C:21]2[C:27]([CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:28][C:19]=1[CH2:18][C:17]1[CH:29]=[CH:30][C:14]([O:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:15]([C:41]2([O:43][C@H:44]([CH2:63][O:64][CH2:65][C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)[C@@H:45]([O:55][CH2:56][C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[C@H:46]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C@H:40]2[O:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[OH:42])[CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 587861482-[4-(Benzyloxy)-3-bromobenzyl]azuleneHCID 178418339Butyllithium

Product 1

HCID 116865651-c-[5-(Azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-o-benzyl-d-glucopyranose
Yield 468.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 1.6 M n-hexane solution of n-butyl lithium (0.32 ml) was added dropwise to a solution of 2-[4-(benzyloxy)-3-bromobenzyl]azulene (0.17 g) in THF (3.0 ml) at −55° C. and the mixture was stirred at the same temperature for 10 minutes. A solution of 2,3,4,6-tetra-O-benzyl-glucono-1,5-lactone (0.12 g) in THF (3.0 ml) was added dropwise to the reaction mixture and the mixture was stirred at the same temperature for 30 minutes. 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 brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 1-C-[5-(azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-O-benzyl-D-glucopyranose (0.9 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-3fc33bf6fb1444a3b4d2d1f959f2521d
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169761B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes