9-dihydrotaxol → Benzaldehyde

HRID 234248Notes

Reaction equation

HRID 234248 reaction equation
[CH3:1][C:2]1[C@@H:18]([O:19][C:20]([C@H:22]([OH:39])[C@@H:23]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:32])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:17][C@:13]2([OH:40])[C:14]([CH3:16])([CH3:15])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C@H:5]([OH:58])[C@@:6]1([CH3:57])[C@H:11]([C@@H:12]2[O:41][C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:43])[C@:10]2([O:52][C:53]([CH3:55])=[O:54])[CH2:50][O:51][C@@H:9]2[CH2:8][C@@H:7]1[OH:56]>C(Cl)Cl>[CH:31](=[O:32])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[CH3:1][C:2]1[C@@H:18]([O:19][C:20]([C@H:22]([OH:39])[C@@H:23]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:32])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:17][C@:13]2([OH:40])[C:14]([CH3:15])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C@H:5]([OH:58])[C@@:6]1([CH3:57])[C@H:11]([C@@H:12]2[O:41][C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:43])[C@:10]2([O:52][C:53]([CH3:55])=[O:54])[CH2:50][O:51][C@@H:9]2[CH2:8][C@@H:7]1[OH:56]

Participants

4

Reactant 1

HCID 30818879-dihydrotaxol

Product 2

HCID 240BenzaldehydeHCID 30818879-dihydrotaxol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 mg of the product of Example 8 were treated with 0. 1 ml benzaldehyde in 0.6 ml methylene chloride to give 1.1 mg of 9-dihydrotaxol-7,9-benzylidene acetal (Scheme 3, compound 12, X=H, Y=Ph).

Sources & evidence

ORD record
ord-53d350a606aa49208bf95ac41ea8e1ae
Source dataset
uspto-grants-1997_01
Patent number
US05594157

Reaction notes

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