(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

Base Information

Chemical Name:(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one
CAS No.:945534-58-7
Molecular Formula:C₂₄H₄₀O₃Si
Molecular Weight:404.665
Hs Code.:

Synonyms:(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

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Chemical Property of (3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

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Technology Process of (3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

There total 1 articles about (3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: (4S,5S,6E)-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 945534-58-7
(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

Guidance literature:: (4S,5S,6E)-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one; t-butyldimethylsiyl triflate; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h; Further stages.;
DOI:10.1039/b701293d

Reference yield: 73.0%

: 945534-58-7
(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

: 276248-85-2
(S)-4-Benzyloxy-3-methoxy-butyraldehyde

: 945534-59-8
(2S,4S,5R,7R,8S,9S,10E)-1-benzyloxy-5-[(tert-butyl)-dimethylsilyloxy]-2-methoxy-4-hydroxy-7,9-dimethyl-8-((1'R)-1'-phenylethoxy)dodec-10-en-6-one

Guidance literature:: (3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one; With chloro-trimethyl-silane; sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

(S)-4-Benzyloxy-3-methoxy-butyraldehyde; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h; Further stages.;
DOI:10.1039/b701293d

Reference yield:

: 945534-58-7
(3R,4S,5S,6E)-1-[(tert-butyl)-dimethylsilyloxy]-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

: 795290-06-1
(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium bis(trimethylsilyl)amide; TMSCl / tetrahydrofuran / 2 h / -78 - 20 °C

1.2: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

2.1: NaHCO₃; ozone / CH₂Cl₂ / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: (+)-B-methoxydiisopinocampheylborane; ozone / diethyl ether; pentane / 3 h / 20 °C

3.2: diethyl ether; pentane / 1 h / -78 °C

3.3: 3.1 g / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: HCl / 3 h / 50 °C

5.1: 810 mg / pyridine / 3 h / 0 - 20 °C

6.1: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

7.1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 6 h / 0 °C

8.1: 177 mg / Ag₂O / dimethylformamide / 20 h / 20 °C

With (+)-Ipc₂BOMe; 1H-imidazole; hydrogenchloride; chloro-trimethyl-silane; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; ozone; silver(l) oxide; potassium hexacyanoferrate(III); potassium osmate(VI); In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; 7.1: Sharpless dihydroxylation;
DOI:10.1039/b701293d