Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

Base Information

Chemical Name:Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester
CAS No.:113892-51-6
Molecular Formula:C₁₉H₂₂O₅Si
Molecular Weight:358.466
Hs Code.:

Synonyms:Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

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Chemical Property of Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

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Technology Process of Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

There total 2 articles about Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester 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:

: 113892-49-2
Benzoic acid (Z)-4-furan-2-yl-4-hydroxy-2-oxo-but-3-enyl ester

: 113892-51-6
Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 3.6 g / diethyl ether / 1 h / 0 °C

2: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min

With triethylamine; In diethyl ether;
DOI:10.1021/ja00220a035

Reference yield:

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 92622-30-5
Benzoic acid (Z)-4-furan-2-yl-4-methoxy-2-oxo-but-3-enyl ester

: 113892-51-6
Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

Guidance literature:: With triethylamine; In diethyl ether; 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min;
DOI:10.1021/ja00220a035

Reference yield:

: 113892-51-6
Benzoic acid (1Z,3Z)-4-furan-2-yl-4-methoxy-2-trimethylsilanyloxy-buta-1,3-dienyl ester

: 113974-10-0
(2S,4S,5S,6R)-4-Benzoyloxy-5-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) Dibal; 2.) DMF; 3.) BF₃*OEt₂; 4.) trifluoroacetic acid

2: ceric chloride heptahydrate, NaBH₄ / CH₂Cl₂; ethanol / 1 h / -78 °C

3: 90 percent / CSA / methanol; benzene / 3 h / 25 °C

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

5: 96 percent / H₂O₂, pyridine / tetrahydrofuran / 4 h / Ambient temperature

6: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO₃ / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h

7: NaHCO₃, Pb(OAc)4 / CH₂Cl₂ / 0.17 h / 0 °C

8: 71 percent / KHMDS, 18-crown-6/acetonitrile complex / tetrahydrofuran; toluene / 0.5 h / -78 °C

9: 1.) OsO₄; 2.) Florisil, NaHSO₃ / 1.) pyridine, -25 deg C, 1 h; 2.) pyridine-THF, roomtemp., 24 h

10: 1.) LiEt₃BH; 2.) DMAP / 1.) THF, 0 deg C, 1 h; 2.) CH₂Cl₂, roomtemp., 8 h

11: 1.) RuO₂*2H₂O, NaIO₄; 2.) NaHCO₃ / 1.) CCl₄-H₂O-CH₃CN, roomtemp., 20 min; 2.) CCl₄-H₂O-CH₃CN, 5 min

12: 62 percent / HF / H₂O; methanol / 4 h / 45 °C

13: K₂CO₃ / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; ceric chloride heptahydrate; boron trifluoride diethyl etherate; hydrogen fluoride; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; sodium hydrogensulfite; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; benzene;
DOI:10.1021/ja00220a035