2-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester → 2-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester

HRID 10148

Reaction equation

HRID 10148 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH:8]([OH:22])[CH2:9][C@H:10]([OH:21])[CH2:11][O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].O[C@H:25]1[CH2:30]C(=O)O[C@H](COC(=O)C2C=CC=CC=2)[CH2:26]1.COC(=O)C[C@H]1C[C@@H](COC(=O)C2C=CC=CC=2)OC(C)(C)O1>>[C:1]([O:5][C:6](=[O:23])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][O:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:21][C:25]([CH3:30])([CH3:26])[O:22]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 210407492-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl esterHCID 21040752(5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl esterHCID 57509267(2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran

Product 1

HCID 101333842-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester

Procedure

89.3%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 8.8%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: undetected.

Sources & evidence

ORD record
ord-3584b565af5c4626b6ea0b0253adc328
Source dataset
uspto-grants-2006_08
Patent number
US07094594B2

Linked notes

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