6-(5-Cholesten-3beta-yloxy)hexyl iodide → 17beta-Carbomethoxy-androst-5-en-3beta-yl 6-iodohexyl ether

HRID 1073541Notes

Reaction equation

HRID 1073541 reaction equation
[I:1]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)CCCC(C)C)C1.S([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:54][C@H:55]1[CH2:72][CH2:71][C@@:70]2([CH3:73])[C:57](=[CH:58][CH2:59][C@@H:60]3[C@@H:69]2[CH2:68][CH2:67][C@@:65]2([CH3:66])[C@H:61]3[CH2:62][CH2:63][C@@H:64]2[C:74]([O:76][CH3:77])=[O:75])[CH2:56]1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O>>[I:1][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:54][C@H:55]1[CH2:72][CH2:71][C@@:70]2([CH3:73])[C:57](=[CH:58][CH2:59][C@@H:60]3[C@@H:69]2[CH2:68][CH2:67][C@@:65]2([CH3:66])[C@H:61]3[CH2:62][CH2:63][C@@H:64]2[C:74]([O:76][CH3:77])=[O:75])[CH2:56]1

Participants

3

Reactant 2

HCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodideHCID 867413646-(17beta-carbomethoxy-androst5-en-3beta-yloxy)-hexyl 1-thio-beta-D-mannopyranoside

Product 1

HCID 6794541017beta-Carbomethoxy-androst-5-en-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 17β-carbomethoxy-androst-5-en-3β-yl 6-iodohexyl ether, there was prepared 6-(17β-carbomethoxy-androst5-en-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-44967498ef404590b9b18d3f53e288da
Source dataset
uspto-grants-1990_11
Patent number
US04970199

Reaction notes

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