HuagongsheHuagongshe Chemistry Print Report · For research reference only
(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate → (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate | HCID 71698666 | — |
| Reactant | (1R,3aS,5aR,5bR,7aR,11aR,11bR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde | HCID 86692373 | — |
| Product | (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate | HCID 86692374 | 71% |
Reaction Steps
The title compound was prepared following the procedure described in method 1 for the preparation of intermediate 1, Step 5, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde as the starting material. (71% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 9.69 (d, J=1.8 Hz, 1H), 5.58 (dd, J=6.7, 2.1 Hz, 1H), 4.89-4.54 (m, 2H), 2.90 (td, J=11.0, 5.8 Hz, 1H), 2.28-2.00 (m, 3H), 2.00-1.64 (m, 7H), 1.60-1.55 (m, 3H), 1.53-1.18 (m, 11H), 1.14 (s, 3H), 1.08 (d, J=7.8 Hz, 1H), 1.03 (s, 3H), 1.00 (s, 3H), 0.97 (s, 3H), 0.93 (s, 3H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906889B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-950e4d37d6c547289fc8a36fe5501fa0 |
| Source note | uspto-grants-2014_12 |