HCID 86594389, compound → HCID 86594390, compound

HRID 1245137Notes

Reaction equation

HRID 1245137 reaction equation
[C:1](=[O:61])([O:3][C@@H:4]([C@@H:55]([CH3:60])/[CH:56]=[CH:57]\[CH:58]=[CH2:59])[C@@H:5]([CH3:54])[C@H:6]([O:44]CC1C=CC(OC)=CC=1)[CH2:7][CH2:8]/[CH:9]=[CH:10]\[C@H:11]([CH3:43])[C@H:12]([O:33]CC1C=CC(OC)=CC=1)[C@@H:13]([CH3:32])/[CH:14]=[CH:15]\[CH2:16][CH2:17][C@H:18]1[C@H:23]([CH3:24])[C@H:22]([O:25][CH2:26][O:27][CH3:28])[C@@H:21]([CH3:29])[C@H:20]([O:30][CH3:31])[O:19]1)[NH2:2].C(=O)(O[C@@H]([C@@H](C)/C=C\C=C)[C@@H](C)[C@H](O)CC/C=C\[C@H](C)[C@H](O)[C@@H](C)/C=C\CC[C@H]1[C@@H](C)[C@H](O)[C@@H](C)C(=O)O1)N>CCOC(C)=O.CCCCCC>[C:1](=[O:61])([O:3][C@@H:4]([C@@H:55]([CH3:60])/[CH:56]=[CH:57]\[CH:58]=[CH2:59])[C@@H:5]([CH3:54])[C@H:6]([OH:44])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[C@H:11]([CH3:43])[C@H:12]([OH:33])[C@@H:13]([CH3:32])/[CH:14]=[CH:15]\[CH2:16][CH2:17][C@H:18]1[C@H:23]([CH3:24])[C@H:22]([O:25][CH2:26][O:27][CH3:28])[C@@H:21]([CH3:29])[C@H:20]([O:30][CH3:31])[O:19]1)[NH2:2]

Participants

4

Reactant 2

HCID 86594389HCID 86594389, compoundHCID 131725991HCID 131725991, compound

Product 1

HCID 86594390HCID 86594390, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Carbamate 39 (4.25 mg, 0.005 mmol) was subjected to the deprotection procedure of PMB described in the preparation of 40. Flash chromatography (EtOAc/hexane 3:2) of the crude product provided 42 (2.8 mg, 92%) as a colorless oil: IR (CHCl3) 3115, 2749, 2328, 1676, 1508, 1215 cm−1; 1H NMR (300 MHz, CDCl3) 6.76 (ddd, 1H, J=16.8, 11.0, 10.1 Hz), 6.18 (t, 1H, J=10.8 Hz), 5.70–5.46 (m, 5H), 5.35 (d, 1H, J=16.8 Hz), 4.49 (dd, J=4.5, 6.6 Hz), 4.82 (d, 2H, J=2.4 Hz), 4.73 (br s, 2H), 4.43 (d, 1H, J=5.1 Hz), 4.15, (m, 1H), 3.78 (m, 1H), 3.56 (s, 3H), 3.54 (s, 3H), 3.36 (t, 2H, J=6.9 Hz), 3.14 (m, 1H), 2.76 (m, 2H), 2.35–2.18 (m, 6H), 2.00–1.60 (m, 7H), 1.22 (d, 3H, J=7.2 Hz), 1.16–1.12 (m, 12H), 1.07 (d, 3H, J=7.2 Hz); 13C NMR (125 MHz, CDCl3) 157.3, 133.7, 133.5, 132.2, 132.0, 130.0, 128.7, 118.0, 109.6, 103.0, 96.5, 82.1, 79.7, 79.1, 72.7, 55.8, 39.9, 39.5, 38.3, 35.5, 35.0, 34.8, 34.6, 30.2, 29.8, 24.3, 18.1, 17.7, 15.7, 15.4, 14.2, 13.2, 8.1; LRMS (ESI) 632.4 (M+Na); HRMS (ESI) calcd for C33H55NO8Na 632.4138, found 632.4139; [α]20D +21.6 (c 0.25, CHCl3).

Sources & evidence

ORD record
ord-8669d8b50124420ab8402c23cc475679
Source dataset
uspto-grants-2006_10
Patent number
US07122686B2

Reaction notes

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