2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester
• CAS No.: 204381-41-9
• Molecular Formula: C₅₉H₈₆O₇Si₂
• Molecular Weight: 963.499

Synonyms:2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

There total 18 articles about 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl 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:

methyl 4-formylbutanoate (6026-86-4) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester (204381-41-9)

Guidance literature:

Multi-step reaction with 8 steps

1: (-)-(1S,2R)-N,N-dibutylnorephedrine / hexane; toluene / 72 h / 0 °C

2: 84 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

3: 94 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

4: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, from 0 to 5 deg C, 20 min, 2.) CH₂Cl₂, from -78 to 0 deg C, 3 h

5: 1.41 g / DMAP / CH₂Cl₂ / 144 h / Ambient temperature

6: 30percent aq. H₂O₂, LiOH / H₂O; tetrahydrofuran; dimethylformamide / 0 °C

7: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature

8: 1.) Me₃SnSnMe₃, (Ph₃P)4Pd, LiCl, 2.) Pd₂(dba)3*CHCl₃, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h

With 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; hexamethyldistannane; diisobutylaluminium hydride; (1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja974010k

Reference yield:

(S)-5-Hydroxy-heptanoic acid methyl ester (118545-01-0) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester (204381-41-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

2: 94 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

3: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, from 0 to 5 deg C, 20 min, 2.) CH₂Cl₂, from -78 to 0 deg C, 3 h

4: 1.41 g / DMAP / CH₂Cl₂ / 144 h / Ambient temperature

5: 30percent aq. H₂O₂, LiOH / H₂O; tetrahydrofuran; dimethylformamide / 0 °C

6: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature

7: 1.) Me₃SnSnMe₃, (Ph₃P)4Pd, LiCl, 2.) Pd₂(dba)3*CHCl₃, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h

With 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; hexamethyldistannane; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja974010k

Reference yield:

13,14β-Dihydro A83543A aglycon 9α,17α-bis-O-(TBDMS) ether (155189-82-5) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester (204381-41-9)

Guidance literature:

Multi-step reaction with 11 steps

1: t-BuOOH, Triton B / methanol; H₂O; tetrahydrofuran / 120 h / Ambient temperature

2: diethyl ether / 0 °C

3: 87 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

4: 85 percent / NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

5: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h

6: 1.) MCPBA, NaHCO₃, 2.) TBAF, 3.) NaIO₄

7: 90 percent / pyridine, DMAP

8: MeOH / 168 h / Heating

9: camphorsulfonic acid / CH₂Cl₂ / 24 h

10: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h

11: 1.) Me₃SnSnMe₃, (Ph₃P)4Pd, LiCl, 2.) Pd₂(dba)3*CHCl₃, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h

With pyridine; methanol; tert.-butylhydroperoxide; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hexamethyldistannane; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/ja974010k

upstream raw materials:

(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl chloride

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-trifluoromethanesulfonyloxy-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

methyl 4-formylbutanoate

(S)-5-Hydroxy-heptanoic acid methyl ester

Downstream raw materials:

spinosyn A

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

(2R,3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone

(3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-3,3a,5a,6,7,8,8a,8b-octahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone pivalate

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