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

Base Information

Chemical Name:methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-(hydroxymethyl)-3-furoate
CAS No.:145474-25-5
Molecular Formula:C₃₃H₃₈O₇Si
Molecular Weight:574.746
Hs Code.:

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

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

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

There total 7 articles about methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-(hydroxymethyl)-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:

: 142468-56-2
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

: 145474-25-5
methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-(hydroxymethyl)-3-furoate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -20 ℃; Yield given;
DOI:10.1021/jo00053a031

Reference yield:

: 126822-60-4
4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester

: 145474-25-5
methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-(hydroxymethyl)-3-furoate

Guidance literature:: Multi-step reaction with 6 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

With sodium tetrahydroborate; sodium periodate; (Me₂Si)2NK; (1S)-10-camphorsulfonic acid; silver perchlorate; tin(IV) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; benzene;
DOI:10.1021/jo00053a031

Reference yield:

: 5-((E)-2-Methyl-3-tributylstannanyl-propenyl)-2-phenylsulfanylmethyl-furan-3-carboxylic acid methyl ester

: 145474-25-5
methyl 5-<(1E)-3-<4-<2-(tert-butyldiphenylsiloxy)ethyl>-2,5-dihydro-5-oxo-2-furyl>-2-methylpropenyl>-2-(hydroxymethyl)-3-furoate

Guidance literature:: Multi-step reaction with 6 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

With sodium tetrahydroborate; sodium periodate; (Me₂Si)2NK; (1S)-10-camphorsulfonic acid; silver perchlorate; tin(IV) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; benzene;
DOI:10.1021/jo00053a031