[(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Base Information

• Chemical Name: [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester
• CAS No.: 625125-02-2
• Molecular Formula: C₃₈H₆₂O₉Si
• Molecular Weight: 690.99

Synonyms:[(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Chemical Property of [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

There total 33 articles about [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl 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:

acetic acid tert-butyl ester (540-88-5) → [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-02-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h

1.2: tetrahydrofuran; hexane / 0.5 h / Heating

2.1: 87.3 g / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol

3.1: camphorsulfonic acid; methanol

4.1: TBAF / tetrahydrofuran

5.1: Et₃N / CH₂Cl₂ / 20 °C

6.1: NaI; NaHCO₃; Na₂SO₃ / butan-2-one / Heating

7.1: Li₂CuCl₄ / tetrahydrofuran

8.1: O₃ / CH₂Cl₂; methanol

8.2: tributylphosphine / CH₂Cl₂; methanol

9.1: LDA / tetrahydrofuran; hexane

9.2: tetrahydrofuran; hexane

10.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

11.1: 59 percent / aq. HCl / acetonitrile

12.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

12.2: tetrahydrofuran; diethyl ether / 0.08 h

13.1: DMAP; Et₃N / CH₂Cl₂ / 1 h

14.1: 2,6-lutidine / CH₂Cl₂ / 0.67 h

15.1: 11.6 g / H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h

16.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 0 °C

17.1: DMAP / CH₂Cl₂ / 14 h

18.1: 9.80 g / ammonium formate; Pd₂(dba)3; Bu₃P / cyclohexane / Heating

With 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; dilithium tetrachlorocuprate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tributylphosphine; camphor-10-sulfonic acid; diethyl methoxy borane; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; sodium iodide; sodium sulfite; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; acetonitrile; butanone; 1.2: Claisen condensation / 16.1: Moffat-Swern oxidation;

DOI:10.1021/ja030316h

Reference yield:

(2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol (604775-07-7) → [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-02-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

2.1: O₃; NaHCO₃ / methanol; CH₂Cl₂

2.2: 51.1 g / dimethyl sulfide / methanol; CH₂Cl₂ / 12 h

3.1: LDA / tetrahydrofuran; hexane

3.2: tetrahydrofuran; hexane

4.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

5.1: 59 percent / aq. HCl / acetonitrile

6.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

6.2: tetrahydrofuran; diethyl ether / 0.08 h

7.1: DMAP; Et₃N / CH₂Cl₂ / 1 h

8.1: 2,6-lutidine / CH₂Cl₂ / 0.67 h

9.1: 11.6 g / H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h

10.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 0 °C

11.1: DMAP / CH₂Cl₂ / 14 h

12.1: 9.80 g / ammonium formate; Pd₂(dba)3; Bu₃P / cyclohexane / Heating

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; cerium(III) chloride; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tributylphosphine; hydrogen; ammonium formate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetonitrile; 10.1: Moffat-Swern oxidation;

DOI:10.1021/ja030316h

Reference yield:

((R)-1-Benzyloxymethyl-3-methyl-but-3-enyloxy)-triethyl-silane → [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-02-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: O₃; NaHCO₃ / methanol; CH₂Cl₂

1.2: 51.1 g / dimethyl sulfide / methanol; CH₂Cl₂ / 12 h

2.1: LDA / tetrahydrofuran; hexane

2.2: tetrahydrofuran; hexane

3.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

4.1: 59 percent / aq. HCl / acetonitrile

5.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

5.2: tetrahydrofuran; diethyl ether / 0.08 h

6.1: DMAP; Et₃N / CH₂Cl₂ / 1 h

7.1: 2,6-lutidine / CH₂Cl₂ / 0.67 h

8.1: 11.6 g / H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h

9.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 0 °C

10.1: DMAP / CH₂Cl₂ / 14 h

11.1: 9.80 g / ammonium formate; Pd₂(dba)3; Bu₃P / cyclohexane / Heating

With 2,6-dimethylpyridine; hydrogenchloride; dmap; cerium(III) chloride; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tributylphosphine; hydrogen; ammonium formate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; acetonitrile; 9.1: Moffat-Swern oxidation;

DOI:10.1021/ja030316h

upstream raw materials:

acetic acid tert-butyl ester

methyl (S)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate

(S)-4-(4-Methoxy-benzyloxy)-3-methyl-butan-2-one

(2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol

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