HCID 86602899, compound → HCID 86602898, compound

HRID 2252498Notes

Reaction equation

HRID 2252498 reaction equation
[Si:1]([O:8][C@@H:9]([CH2:35][C@H:36]([OH:63])[C:37]#[C:38][C@H:39]([CH3:62])[C@H:40]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[C@@H:41]([CH3:53])[CH2:42][CH2:43][CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[C@H:10]([CH3:34])/[CH:11]=[CH:12]/[CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Si:1]([O:8][C@@H:9]([CH2:35][C@H:36]([OH:63])/[CH:37]=[CH:38]\[C@H:39]([CH3:62])[C@H:40]([O:54][Si:55]([C:58]([CH3:59])([CH3:61])[CH3:60])([CH3:57])[CH3:56])[C@@H:41]([CH3:53])[CH2:42][CH2:43][CH2:44][O:45][Si:46]([C:49]([CH3:50])([CH3:51])[CH3:52])([CH3:48])[CH3:47])[C@H:10]([CH3:34])/[CH:11]=[CH:12]/[CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86602899HCID 86602899, compound

Product 1

HCID 86602898HCID 86602898, compoundYield 100,367.203%

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

The procedure for 34 was used with alkyne 65 (1.69 g, 1.85 μmol) and Lindlar catalyst (ca. 200 mg) to yield 66 (1.70 g, quantitative) as a pale yellow oil: IR (CHCl3) 3477, 2955, 2856, 1471, 1448, 1386, 1254, 1057, 835, 773, 705 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.63-7.60 (m, 6H), 7.43-7.27 (m, 9H), 5.88-5.77 (m, 2H), 5.70 (t, J=10.1 Hz, 1H), 5.49 (dd, J=10.6, 8.4 Hz, 1H), 4.78 (m, 1H), 4.06 (m, 1H), 3.76-3.72 (m, 4H), 3.58 (t, J=3.6 Hz, 1H), 2.89 (m, 1H), 2.63 (m, 1H), 2.20 (d, J=2.8 Hz, 1H), 1.73-1.48 (m, 7H), 1.18 (d, J=6.9 Hz, 3H), 1.15 (d, J=7.0 Hz, 3H), 1.08-1.02 (m, 27H), 0.29-0.20 (m, 18H); 13C NMR (75 MHz, CDCl3) δ 144.3, 134.9, 134.4, 131.5, 128.6, 127.7, 127.0, 126.8, 86.7, 79.8, 72.8, 65.0, 64.7, 63.5, 42.1, 39.7, 37.9, 35.9, 31.4, 29.9, 26.2, 26.0, 25.9, 20.1, 18.4, 18.3, 18.0, 14.9, 14.5, −3.6, −3.8, −4.5, −4.6, −5.3; LRMS (ESI) 937.5 [M+Na]+; HRMS (ESI) calcd for C55H90O5Si3Na 937.5994 [M+Na]+, found 937.6016; [α]20D+2.1 (c 0.92, CHCl3).

Sources & evidence

ORD record
ord-495c6e41dc89404aa9e9268c2bf6ff1d
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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