methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate

Base Information

• Chemical Name: methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate
• CAS No.: 145474-28-8
• Molecular Formula: C₃₇H₄₃BrO₆Si
• Molecular Weight: 691.734

Synonyms:methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate

Chemical Property of methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate

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Technology Process of methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate

There total 10 articles about methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate 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: 64.0%

methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-<(2E)-3-methyl-4-<(tetrahydro-2H-pyran-2-yl)oxy>-2-butenyl>-3-furoate (145474-27-7) → methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate (145474-28-8)

Guidance literature:

With bromine; 1,2-bis-(diphenylphosphino)ethane; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo00053a031

Reference yield:

4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester (126822-60-4) → methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate (145474-28-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) SnCl₄ / 1) THF, CH₂Cl₂, -78 deg C, 5 min, 2) RT, 90 min

2: 2) 10-camphorsulfonic acid / 1) benzene, reflux, Dean-Stark-conditions, 1h, 2) 2h

3: 1) (Me₂Si)2NK / 1) THF, toluene, -78 deg C, 45 min, 2) -78 deg C, 2 h

4: AgClO₄ / benzene; H₂O / 1 h

5: NaIO₄, NaHCO₃ / methanol; H₂O; tetrahydrofuran / 5 h

6: NaBH₄ / tetrahydrofuran; methanol / -20 °C

7: 95 percent / N-bromosuccinimide, dimethyl sulfide / CH₂Cl₂ / 2 h / Ambient temperature

8: 65 percent / Pd(PPh₃)4 / CHCl₃ / 48 h / Heating

9: 64 percent / 1,2-bis(diphenylphosphino)ethane, bromine / CH₂Cl₂ / 2 h / 0 °C

With sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; dimethylsulfide; (Me₂Si)2NK; (1S)-10-camphorsulfonic acid; bromine; silver perchlorate; tin(IV) chloride; sodium hydrogencarbonate; 1,2-bis-(diphenylphosphino)ethane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; benzene;

DOI:10.1021/jo00053a031

Reference yield:

5-((E)-2-Methyl-3-tributylstannanyl-propenyl)-2-phenylsulfanylmethyl-furan-3-carboxylic acid methyl ester → methyl 2-<(2E)-4-bromo-3-methyl-2-butenyl>-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate (145474-28-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) SnCl₄ / 1) THF, CH₂Cl₂, -78 deg C, 5 min, 2) RT, 90 min

2: 2) 10-camphorsulfonic acid / 1) benzene, reflux, Dean-Stark-conditions, 1h, 2) 2h

3: 1) (Me₂Si)2NK / 1) THF, toluene, -78 deg C, 45 min, 2) -78 deg C, 2 h

4: AgClO₄ / benzene; H₂O / 1 h

5: NaIO₄, NaHCO₃ / methanol; H₂O; tetrahydrofuran / 5 h

6: NaBH₄ / tetrahydrofuran; methanol / -20 °C

7: 95 percent / N-bromosuccinimide, dimethyl sulfide / CH₂Cl₂ / 2 h / Ambient temperature

8: 65 percent / Pd(PPh₃)4 / CHCl₃ / 48 h / Heating

9: 64 percent / 1,2-bis(diphenylphosphino)ethane, bromine / CH₂Cl₂ / 2 h / 0 °C

With sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; dimethylsulfide; (Me₂Si)2NK; (1S)-10-camphorsulfonic acid; bromine; silver perchlorate; tin(IV) chloride; sodium hydrogencarbonate; 1,2-bis-(diphenylphosphino)ethane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; benzene;

DOI:10.1021/jo00053a031

upstream raw materials:

methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-<(2E)-3-methyl-4-<(tetrahydro-2H-pyran-2-yl)oxy>-2-butenyl>-3-furoate

4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester

5-((E)-3-{4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-oxo-2,5-dihydro-furan-2-yl}-2-methyl-propenyl)-2-formyl-furan-3-carboxylic acid methyl ester

methyl 2-(bromomethyl)-5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-3-furoate

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