Carbon Tetrachloride → HCID 68508363, compound
Reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@@:10]21[C:51]1[S:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:52]O)[C:43]=1[CH2:42][CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)[Cl:55].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@@:10]21[C:51]1[S:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:52][Cl:55])[C:43]=1[CH2:42][CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3,3′,4,4′,5′,6′-hexahydro-8-hydroxymethyl-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran] (72 mg, 0.10 mmol) in dichloromethane (1 mL) were added carbon tetrachloride (48 μL, 0.5 mmol) and triphenylphosphine (131 mg, 0.5 mmol). The resultant solution was then stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2)), to thereby obtain the titled compound (42 mg, 48%).
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2))
Sources & evidence
- ORD record
- ord-17b27085e36c46da928b66cc6cf538e9
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207134B2
Reaction notes
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