Potassium Carbonate → HCID 86602787, compound

HRID 2220058Notes

Reaction equation

HRID 2220058 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6](O)[CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([C@:50]2([O:68][C@H:67]([CH2:69][O:70][C:71](=[O:73])[CH3:72])[C@@H:62]([O:63][C:64](=[O:66])[CH3:65])[C@H:57]([O:58][C:59](=[O:61])[CH3:60])[C@H:52]2[O:53][C:54](=[O:56])[CH3:55])[OH:51])=[CH:46][C:45]=1[OH:74].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([C@:50]2([O:68][C@H:67]([CH2:69][O:70][C:71](=[O:73])[CH3:72])[C@@H:62]([O:63][C:64](=[O:66])[CH3:65])[C@H:57]([O:58][C:59](=[O:61])[CH3:60])[C@H:52]2[O:53][C:54](=[O:56])[CH3:55])[OH:51])=[CH:46][C:45]=1[O:74][CH:6]1[CH2:7][CH2:8][CH:3]([O:2][CH3:1])[CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1403324-Methoxycyclohexanol (cis,trans)HCID 86602788HCID 86602788, compound

Product 1

HCID 86602787HCID 86602787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.08 g 4-methoxycyclohexanol, 0.16 g triphenylphosphine and 0.12 ml diisopropyl azodicarboxylate are added to a solution of 0.25 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-hydroxy-benzene in 3 ml of tetrahydrofuran, in the order stated. The solution is stirred for 14 h at ambient temperature and then combined with aqueous potassium carbonate solution. Then it is extracted with ethyl acetate, dried over sodium sulphate and the solvent is removed. The residue is purified on silica gel (cyclohexane/ethyl acetate 7:3->1:1).

Workup

  1. extractionThen it is extracted with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. customthe solvent is removed
  4. customThe residue is purified on silica gel (cyclohexane/ethyl acetate 7:3->1:1)

Sources & evidence

ORD record
ord-46a3bcc531084acfbf2a572ab74605b5
Source dataset
uspto-grants-2008_08
Patent number
US07417032B2

Reaction notes

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