Boron trifluoride etherate → HCID 54193385, compound

HRID 1583819Notes

Reaction equation

HRID 1583819 reaction equation
B(F)(F)F.CCOCC.[C:10]([NH:13][C@H:14]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@@H:15]1OC(=O)C)(=[O:12])[CH3:11].[CH2:37]([SH:46])[CH:38]=[CH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)(Cl)Cl>[C:10]([NH:13][C@H:14]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@@H:15]1[S:46][CH2:37][CH:38]=[CH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 989180HCID 989180, compoundHCID 537005513-Phenylprop-2-ene-1-thiol

Product 1

HCID 54193385HCID 54193385, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Boron trifluoride etherate (200 μl, 1.3 mmol) is added to a solution of 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-mannopyranose (389 mg) and cinnamyl mercaptan (150 mg) in chloroform (10 ml), and the solution is kept under nitrogen for 2 days. Another portion of boron trifluoride etherate (200 μl) is added and the solution is kept under nitrogen for another 2 days. Chloroform (15 ml) is added and the solution is washed with aqueous sodium hydrogencarbonate and water, dried, and evaporated in vacuo to a residue, which is purified by preparative chromatography (EtOAc--CHCl3, 10:90, v/v, as a developing phase) to give the title compound (250 mg, 52%).

Workup

  1. waitthe solution is kept under nitrogen for another 2 days
  2. washthe solution is washed with aqueous sodium hydrogencarbonate and water
  3. customdried
  4. customevaporated in vacuo to a residue, which
  5. customis purified by preparative chromatography (EtOAc

Sources & evidence

ORD record
ord-a7a12d290f6a496cb020132ee9729432
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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