6-(5-Cholesten-3beta-yloxy)hexyl iodide → Stigmasta-5,22-dien-3beta-yl 6-iodohexyl ether

HRID 1073539Notes

Reaction equation

HRID 1073539 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:10]1.S(CCCCCCO[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)C=C[C@H](C(C)C)CC)C1)[C@@H:37]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H:38]1O>>[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH:20]=[CH:21][C@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:37][CH3:38])[CH2:10]1

Participants

3

Reactant 2

HCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodideHCID 867413616-(stigmasta-5,22-dien-3beta-yloxy)hexyl 1-thio-beta-D-mannopyranoside

Product 1

HCID 86741360Stigmasta-5,22-dien-3beta-yl 6-iodohexyl ether

Procedure

Employing the procedure substantially as described in Example 2, but substituting for cholest-5-en-3β-yl 6-iodohexyl ether, an equivalent amount of stigmasta-5,22-dien-3β-yl 6-iodohexyl ether, there was prepared 6-(stigmasta-5,22-dien-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside (Step D). TLC data and Rf values are given in the above Table.

Sources & evidence

ORD record
ord-92a8d18ad2c74e5f8e158c8afaff64b1
Source dataset
uspto-grants-1990_11
Patent number
US04970199

Reaction notes

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