Hydrogen Peroxide → HCID 69956726、化合物

反応式

[CH3:1][O:2][C@H:3]1[C@@H:7]2[CH2:8][C@H:9]3[C@H:14]([C:15](=[CH2:16])[C@@H:6]2[C@@H:5]([CH3:17])[O:4]1)[CH2:13][CH2:12][CH2:11][CH2:10]3.[OH:18]O.[OH-:20].[Na+]>>[OH:18][CH2:16][C@@H:15]1[C@H:6]2[C@H:7]([C@H:3]([O:2][CH3:1])[O:4][C@@H:5]2[CH3:17])[CH2:8][C@H:9]2[C@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2.[OH:20][CH2:16][C@H:15]1[C@H:6]2[C@H:7]([C@H:3]([O:2][CH3:1])[O:4][C@@H:5]2[CH3:17])[CH2:8][C@H:9]2[C@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2

参加物

反応物 3

HCID 784Hydrogen Peroxide

HCID 14798Sodium Hydroxide

HCID 69957465HCID 69957465、化合物

生成物 2

HCID 69956726HCID 69956726、化合物収率 75%

HCID 69957181HCID 69957181、化合物収率 8%

実験手順

Similarly to Example 8, after 663.7 mg(2.81 mmol) of (1R,3R,3aR,4aR,8aS,9aR)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan were reacted with 4.21 ml (1.5 equivalents) of borane-tetrahydrofuran complex(1M), it was oxidized by adding 3.00 ml of 30% hydrogen peroxide solution and 3.00 ml of 10% aqueous solution of sodium hydroxide to obtain 538.2 mg of (1R,3R,3aS,4S,4aR,8aS,9aR)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan(yield 75%) and 55.2 mg of (1R,3R,3aS,4R,4aR,8aS,9aR)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan(8%). (1R,3R,3aS,4S,4aR,8aS,9aR)-4-hydoxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan