Diiodomethane → HCID 52914479, compound

HRID 1944079Notes

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:12](=[CH2:31])[O:11][C@H:10]1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH3:48])=[CH:42][CH:41]=2)[CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:49]CCCCC.ICI>C(OCC)C.C([Zn]CC)C.O.C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2([CH2:49][CH2:31]2)[O:11][C@H:10]1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH3:48])=[CH:42][CH:41]=2)[CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (2S,3S,4R,5S)-3,4,5-tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran (150 mg, 0.22 mmole) in dry diethyl ether (3 mL), 1.0M diethylzinc in hexane (1.2 mL, 1.2 mmole), diiodomethane (0.1 mL, 1.2 mmole) was added at room temperature and stirred at 40° C. in sealed vessel for 8 hours. The reaction mixture was diluted with water (20 mL) and saturated aqueous sodium bicarbonate (3 ml) and extracted with DCM (2×30 mL). The crude product was purified by silica gel column chromatography (2% ethyl acetate in hexane) to furnish 105 mg of (5S,6S,7R,8S)-6,7,8-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane.

Workup

extractionextracted with DCM (2×30 mL)
customThe crude product was purified by silica gel column chromatography (2% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-ac5f695b8eaa4c75a9c5f3b0e667e0e6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394772B2

Reaction notes

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