Diazabicyclo(2.2.2)octane → 1-Propenyl 3-O-benzyl-2-deoxy-2-palmitamido-beta-D-glucopyranoside

HRID 2413046Notes

Reaction equation

HRID 2413046 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][OH:21])[O:16][C@@H:11]([O:12][CH2:13][CH:14]=[CH2:15])[C@@H:10]1[NH:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCC(CC1)CN2>C(O)C.C1C=CC=CC=1.O.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][OH:21])[O:16][C@@H:11]([O:12][CH:13]=[CH:14][CH3:15])[C@@H:10]1[NH:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 136165Diazabicyclo(2.2.2)octaneHCID 18595873allyl 3-O-benzyl-2-deoxy-2-palmitamido-beta-D-glucopyranoside

Product 1

HCID 539067701-Propenyl 3-O-benzyl-2-deoxy-2-palmitamido-beta-D-glucopyranoside

Reagents, catalysts & solvents 2

HCID 178479813HCID 178479813, compoundCatalystHCID 66847609Benzene ethanol waterSolvent

Procedure

To a solution of Compound 5 (3.2 g., 5.84 mmol) in ethanol:benzene:water (7:3:1, v/v) (250 ml.) were added diazabicyclo[2.2.2]octane (0.2 g, 1.8 mmol) and tris(triphenylphosphine) rhodium(I) chloride (0.4 g., 0.43 mmol). The mixture was stirred for 24 h. under reflux. Solvents were evaporated and coevaporated with toluene. A portion of the product, purified on a column of silica gel, afforded an amorphous solid, [α]D25 -7.4°, [α]43625 -13/3° (chloroform).

Workup

  1. temperatureunder reflux
  2. customSolvents were evaporated
  3. customA portion of the product, purified on a column of silica gel
  4. customafforded an amorphous solid, [α]D25 -7.4°, [α]43625 -13/3° (chloroform)

Sources & evidence

ORD record
ord-7822d699e843406f852d14bb930e477e
Source dataset
uspto-grants-1985_01
Patent number
US04495346

Reaction notes

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