methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate

Base Information

• Chemical Name: methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate
• CAS No.: 802912-21-6
• Molecular Formula: C₂₇H₃₈O₆SSi
• Molecular Weight: 518.747
• Mol file: 802912-21-6.mol

Synonyms:methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate

Chemical Property of methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate

There total 14 articles about methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate 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: 95.0%

methanesulfonyl chloride (124-63-0) + methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-hydroxycyclopentaneacetate (802911-68-8) → methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate (802912-21-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1002/hlca.200490202

Reference yield:

ethyl (1R,2R,3S,4S,5R)-7-oxo-6-oxatricyclo[3.3.1.02,4]nonane-3-carboxylate → methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate (802912-21-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: HCl; water / 48 h / Heating

1.2: 5.29 g / pyridinium chlorochromate / CH₂Cl₂ / 2 h

2.1: 91 percent / H₂ / Pd/C / methanol / 15 h / 20 °C / 760 Torr

3.1: 92 percent / NaBH₄ / methanol / 1 h / 0 °C

4.1: 64 percent / Pb₃O₄ / 1 h / 190 - 200 °C / 150.01 Torr

5.1: BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

5.2: 27 percent / tetrahydrofuran; hexane / 2 h / 0 °C

6.1: 60 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 760 Torr

7.1: 47 percent / BH₃ / tetrahydrofuran / 7 h / 0 °C

8.1: 90 percent / HCl; water / 20 h / Heating

9.1: 74 percent / 1H-imidazole / dimethylformamide / 40 h / 20 °C

10.1: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; lead(II,IV) oxide; borane; water; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490202

Reference yield:

ethyl (1R,2R,3S,4R,5R)-6-oxotricyclo[3.2.1.02,4]octane-3-carboxylate (802911-57-5) → methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-[(methylsulfonyl)oxy]cyclopentaneacetate (802912-21-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 89 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 20 h / 20 °C

2.1: HCl; water / 48 h / Heating

2.2: 5.29 g / pyridinium chlorochromate / CH₂Cl₂ / 2 h

3.1: 91 percent / H₂ / Pd/C / methanol / 15 h / 20 °C / 760 Torr

4.1: 92 percent / NaBH₄ / methanol / 1 h / 0 °C

5.1: 64 percent / Pb₃O₄ / 1 h / 190 - 200 °C / 150.01 Torr

6.1: BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

6.2: 27 percent / tetrahydrofuran; hexane / 2 h / 0 °C

7.1: 60 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 760 Torr

8.1: 47 percent / BH₃ / tetrahydrofuran / 7 h / 0 °C

9.1: 90 percent / HCl; water / 20 h / Heating

10.1: 74 percent / 1H-imidazole / dimethylformamide / 40 h / 20 °C

11.1: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; lead(II,IV) oxide; borane; water; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Baeyer-Villiger oxidation;

DOI:10.1002/hlca.200490202

upstream raw materials:

methanesulfonyl chloride

methyl (1R,2S,4S)-2-{2-{[(tert-butyl)diphenylsilyl]oxy}ethyl}-4-hydroxycyclopentaneacetate

(1R,4R,5R)-5-(2-hydroxyethyl)bicyclo[2.2.1]heptan-2-one

(1R,5R,6R)-6-(2-hydroxyethyl)-2-oxabicyclo[3.2.1]octan-3-one

Refernces