ChemicalBook CAS DataBase List ((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane) synthesis

7synthesis methods

Product Name:((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)
CAS Number:957214-02-7
Molecular formula:C35H66O4Si2
Molecular Weight:607.07

(1R,3aR,7aR)-1-[(1S)-2,2-DiMethoxy-1-Methylethyl]octahydro-7a-Methyl-4H-inden-4-one

957214-01-6
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$95.00/250mg

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)

957214-02-7
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Yield:957214-02-7 69%

Reaction Conditions:

Stage #1: (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexanewith sodium hexamethyldisilazane in tetrahydrofuran at -78 - 0; for 0.0833333 h;
Stage #2: (1R,3aR,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-one in tetrahydrofuran at -78 - 20; for 1.5 h;

Steps:

In a flame dried round bottom flask, cooled to -78 ⁰C under argon, NaHMDS (2.574 mmol) was added to a solution of 16 (1.469 g, 2.574 mmol) in THF (30 ml_). The reaction vessel was suspended above the ice bath for 5 min, then recooled to -78 ⁰C. A solution of 18 (0.6235 g, 2.451 mmol) in THF (10 ml.) was cannulated into the reaction mixture over a period of 15 min. The reaction mixture was left to stir at -78 ⁰C for 1 h, followed by warming to room temperature over a period of 30 min, and quenching with sat. NH₄CI (25 ml_). The layers were separated and the aqueous layer extracted with EtOAc (2 x 25mL). The organic layers were combined and extracted with sat. NH₄CI (2 x 25 ml_), distilled H₂O (25 mL) and brine (25 ml_), then dried (MgSO₄) and concentrated in vacuo to give the crude product. Compound 19 was isolated via FCC (20% EtOAc in hexanes) as a clear amorphous solid in 69% yield (1.027 g, 1.691 mmol). R_f = 0.70 (10% EtOAc in hexanes); ¹H NMR (300 MHz, CDCI₃) δ 6.16 (1 H, d, J = 11.0 Hz), 5.82 (1 H, d, J = 11.0 Hz), 4.15 (1 H, d, J = 2.0 Hz), 4.13-4.02 (2H, m), 3.45 (3H, s), 3.39 (3H, s), 2.88-2.76 (1 H, m), 2.46-2.33 (2H, m), 2.30-2.22 (1 H, m), 2.16-1.50 (13H, m), 1.44-1.34 (2H, m), 0.98 (3H, d, J = 6.5 Hz), 0.89 (9H, s), 0.88 (9H, s), 0.56 (3H, s), 0.07 (12H, m); ¹³C NMR (75 MHz, CDCI₃) δ 140.6, 133.8, 121.8, 116.3, 109.2, 68.3, 68.2, 57.2, 56.0, 55.9, 52.5, 46.2, 46.0, 44.0, 40.7, 40.1 , 37.1 , 29.0, 27.4, 26.1 (6C), 23.6, 22.6, 18.4 (2C), 12.3, 12.2, -4.3, -4.4, - 4.5, -4.6; IR (film) v 2951 , 1739, 1619, 1471 , 1361 , 1254, 1187, 1089, 1026, 960, 921 , 836 cm^"1; LRMS (El): m/z (rel. intensity) = 608 (10), 607 (20, M⁺), 592 (12), 590 (22), 576 (21), 575 (51), 574 (100), 534 (8), 533 (19), 518 (9), 458 (59), 442 (96), 239 (13), 237 (11); HRMS (El): m/z calcd. for (M⁺) = 606.4499, found = 606.4490.