2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester
• CAS No.: 119618-99-4
• Molecular Formula: C₄₂H₅₇IO₅Si
• Molecular Weight: 796.902

Synonyms:2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester

There total 15 articles about 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl 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:

{(1S,2S,3R)-3-((S)-4-Benzyloxy-1-methyl-butyl)-1-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentylmethoxy}-tert-butyl-diphenyl-silane (119619-00-0) → 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester (119618-99-4)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

2: pyridine / Ambient temperature

3: n-Bu₄NF / dimethylformamide / 50 °C

4: Swern oxidation

5: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

6: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

7: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

8: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

9: Swern oxidation

With pyridine; dmap; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00189a069

Reference yield:

{(1S,4S,5S)-4-((S)-4-Benzyloxy-1-methyl-butyl)-1-methyl-5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enylmethoxy}-tert-butyl-diphenyl-silane (119594-26-2) → 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester (119618-99-4)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

2: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

3: pyridine / Ambient temperature

4: n-Bu₄NF / dimethylformamide / 50 °C

5: Swern oxidation

6: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

7: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

8: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

9: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

10: Swern oxidation

With pyridine; dmap; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00189a069

Reference yield:

(S)-5-Benzyloxy-2-{(1S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enyl}-pentan-1-ol (119594-24-0) → 2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-3-methyl-2-(2-oxo-ethyl)-cyclopentyl]-pentyl ester (119618-99-4)

Guidance literature:

Multi-step reaction with 12 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: LiAlH₄ / diethyl ether / Ambient temperature

3: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

4: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

5: pyridine / Ambient temperature

6: n-Bu₄NF / dimethylformamide / 50 °C

7: Swern oxidation

8: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

9: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

10: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

11: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

12: Swern oxidation

With pyridine; dmap; lithium aluminium tetrahydride; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00189a069

upstream raw materials:

2,2-Dimethyl-propionic acid (S)-4-[(1R,2S,3S)-3-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-2-(2-hydroxy-ethyl)-3-methyl-cyclopentyl]-pentyl ester

2,2-Dimethyl-propionic acid (S)-4-{(1R,2S,3S)-3-hydroxymethyl-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentyl ester

2,2-Dimethyl-propionic acid (S)-4-{(1R,2S,3S)-3-formyl-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentyl ester

(S)-4-{(1R,2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentan-1-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (S)-4-[(E)-(3R,3aS,6aR,7R,10aS)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-10a-methyl-6-methylene-9-oxo-1,2,3,3a,4,5,6,6a,7,8,9,10a-dodecahydro-dicyclopenta[a,d]cycloocten-3-yl]-pentyl ester

Ophiobolin C

(S)-4-[(E)-(3R,3aS,6aS,7R,9R,9aS,10aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-9,10a-dimethyl-1,2,3,3a,4,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-3-yl]-pentanal

(E)-(1R,3R,3aS,6aS,7R,9aR,10aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-7-((S)-1,5-dimethyl-hex-4-enyl)-1,9a-dimethyl-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-1-ol

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