HCID 131727358, compound → HCID 131727357, compound

HRID 1784167Notes

Reaction equation

HRID 1784167 reaction equation
[C:1]1([S:7]([C@H:10]2[C@H:16]3[C@H:14]([O:15]3)[CH2:13][C@H:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C@@H:11]2[CH:25](C)C)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)(Cl)Cl>[C:1]1([S:7]([C@H:10]2[C@H:16]3[C@H:14]([O:15]3)[CH2:13][C@H:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[C@@H:11]2[CH3:25])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 131727358HCID 131727358, compound

Product 1

HCID 131727357HCID 131727357, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1H NMR (CDCl3): δ 7.91 (m, 2H), 7.62 (m, 3H), 4.15 (ddd, J=10.4 Hz, 6.3 Hz, 4.4 Hz, 1H), 3.59 (d, J=2.4 Hz, 1H), 3.35 (d, J=3.5 Hz, 1H), 3.25 (dd, J=5.0 Hz, 4.3 Hz, 1H), 2.32 (m, 1H), 1.98 (m, 2H), 1.01 (d, J=7.2 Hz, 3H), 0.86 (s, 9H), 0.05 (s, 6H). 13C NMR (CDCl3): □138.3 134.0, 129.4, 128.4, 65.7, 65.3, 52.1, 49.4, 31.8, 28.5, 14.1, −4.8, −4.9. LRMS: (CI) highest mass 383 (M+H), base peak 383. HRMS: (CI) calculated for C19H30O4SSi 383.1712, found 383.1700. [α]D (c 5.0, CHCl3)=+16°. (1R, 3S, 4S, 5R, 6R)-(5-Benzenesulfonyl-4-isopropyl-7-oxa-bicyclo[4.1.0]hept-3-yloxy)-tert-butyldimethylsilane 23b Pr Quantitative yield. 1H NMR (CDCl3): δ7.93 (m, 2H), 7.64 (m, 3H), 4.41 (ddd, J=11.1 Hz, 6.9 Hz, 4.3 Hz, 1H), 3.84 (m, 1H), 3.42 (m, 1H), 3.31 (m, 1H), 1.98 (m, 4H), 0.91 (d, J=6.6 Hz, 3H), 0.88 (s, 9H), 0.66 (d, J=6.4 Hz, 3H), 0.11 (s, 3H), 0.10 (s, 3H). 13C NMR (CDCl3): δ138.3, 134.0, 129.4, 128.5, 67.0, 62.6, 52.5, 48.8, 42.6, 29.0, 26.9, 25.8, 23.5, 22.0, 17.9, −4.7, −5.0. LRMS: (CI) highest mass 411 (M+H), base peak 137 HRMS: (CI) calculated for C21H34O4SSi 411.2025, found 411.2005. [α]D (c 38.0, CHCl3)=−1°.

Sources & evidence

ORD record
ord-92ca338d45f34950ac71e0f1069d5ed8
Source dataset
uspto-grants-2009_03
Patent number
US07501535B2

Reaction notes

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