2,6-Lutidine → HCID 86602901, compound

HRID 2252499Notes

Reaction equation

HRID 2252499 reaction equation
[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]([CH3:61])([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].[Si:64](OS(C(F)(F)F)(=O)=O)([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65].N1C(C)=CC=CC=1C>CCOC(C)=O.CCCCCC>[Si:1]([O:8][C@@H:9]([CH2:35][C@H:36]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])/[CH:37]=[CH:38]\[C@H:39]([CH3:62])[C@H:40]([O:54][Si:55]([C:58]([CH3:60])([CH3:59])[CH3:61])([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

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86602898HCID 86602898, compound

Product 1

HCID 86602901HCID 86602901, compoundYield 95,529.898%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The procedure for 35 was used with alcohol 66 (1.70 g, 1.85 μmol), TBSOTf (0.94 mL, 4.07 mmol) and 2,6-lutidine (0.51 mL, 4.44 mmol) to yield 67 (1.82 g, 96%) by flash column chromatography (EtOAc/hexane 1:19) as a colorless oil: IR (CHCl3) 2956, 2856, 1471, 1448, 1254, 1092, 1004, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.77-7.75 (m, 6H), 7.57-7.47 (m, 9H), 6.02-5.87 (m, 2H), 5.76 (t, J=10.8 Hz, 1H), 5.61 (dd, J=10.8, 8.5 Hz, 1H), 4.88 (m, 1H), 4.24 (m, 1H), 3.88 (m, 4H), 3.75 (m, 1H), 2.94 (m, 1H), 2.73 (m, 1H), 1.83 (m, 2H), 1.75 (m, 2H), 1.57 (m, 1H), 1.46-1.41 (m, 2H), 1.31 (d, J=6.8 Hz, 3H), 1.30(d, J=6.3 Hz, 3H), 1.24-1.13 (m, 39H), 0.44-0.34 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 144.4, 134.4, 132.9, 132.2, 128.7, 127.7, 126.8, 86.8, 80.2, 72.3, 66.6, 65.1, 63.6, 42.4, 41.6, 38.4, 35.7, 31.6, 29.9, 26.3, 26.0, 19.6, 18.5, 18.4, 18.2, 15.1, 13.2, −2.9, −3.6, −3.7, −4.2, −5.2; LRMS (ESI) 1051.6 [M+Na]+, 918.6, 769.5, 637.4, 413.2; HRMS (ESI) calcd for C61H104O5Si4Na 1051.6859 [M+Na]+, found 1051.6848 [α]20D−8.3 (c 2.4, CHCl3).

Sources & evidence

ORD record
ord-c0496bc4513d4467a94f300cc20366c3
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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