HCID 11734259, compound → HCID 18607341, compound

HRID 543025Notes

Reaction equation

S(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[CH:27]=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C@@H:17]([OH:31])[CH2:16][CH2:15]1)(C)(=O)=O.[Br-].C[Si](C)(C(C)(C)C)OCCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:65]([S:70][CH2:71][CH2:72][CH2:73][SH:74])[CH2:66][CH2:67][CH2:68][CH3:69]>>[CH2:65]([S:70][CH2:71][CH2:72][CH2:73][S:74][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:29][C:28]2[CH:27]=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[C@@H:22]2[C@@H:13]1[C@H:14]1[C@@:18]([CH2:20][CH2:21]2)([CH3:19])[C@@H:17]([OH:31])[CH2:16][CH2:15]1)[CH2:66][CH2:67][CH2:68][CH3:69]

Participants

Reactant 3

HCID 11734259HCID 11734259, compound

HCID 20206835HCID 20206835, compound

HCID 53951426HCID 53951426, compound

Product 1

HCID 18607341HCID 18607341, compound

Procedure

The process described in Example 32 was repeated using 7α-(6-mesyloxyhexyl)oestra-1,3,5(10)-triene-3,17β-diol (obtained as described in Example 41 using initially 5-(dimethyl-t-butylsilyloxy)pentyltriphenylphosphonium bromide and 3-n-pentylthiopropanethiol (obtained from trimethylene-1,3-dithiol and pentyl bromide) as starting materials. There was thus obtained as an oil 7α-[6-(3-n-pentylthiopropylthio)hexyl]-oestra-1,3,5(10)triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

customobtained

Sources & evidence

ORD record: ord-a289ec252e9b4d9bba73f88edb02d84e
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659516

Reaction notes

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