(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:710336-69-9
Molecular Formula:C₂₇H₄₇NO₆
Molecular Weight:481.673
Hs Code.:

Synonyms:(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 22 articles about (R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic 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: 99.0%

: (R)-5-((S)-6-{(1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,2-dimethyl-6-oxo-cyclohexyl}-2-methyl-4-oxo-hexyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 710336-69-9
(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2004.02.064

Reference yield:

: 241155-56-6
(E)-(S)-4-Methyl-5-triisopropylsilanyloxy-pent-2-en-1-ol

: 710336-69-9
(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 90 percent / t-BuOOH; Ti(O-i-Pr)4; diethyl L-(+)-tartrate / molecular sieves 4A / CH₂Cl₂ / -20 °C

2.1: 96 percent / DIBAL-H / toluene / 0 °C

3.1: Et₃N; DMAP / CH₂Cl₂

4.1: NaN₃ / dimethylformamide

5.1: H₂ / Pd/C / tetrahydrofuran

6.1: NaOH

7.1: 96 percent / p-TsOH / benzene

8.1: 95 percent / TBAF / tetrahydrofuran

9.1: 91 percent / n-Bu₃P; pyridine

10.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 93 h / 0 °C

11.1: n-BuLi / tetrahydrofuran / -78 °C

11.2: tetrahydrofuran

12.1: Dess-Martin periodinane; pyridine / CH₂Cl₂

13.1: 79 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

14.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

15.1: 99 percent / TBAF / tetrahydrofuran

With pyridine; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; sodium hydroxide; n-butyllithium; sodium azide; samarium diiodide; diethyl (2R,3R)-tartrate; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 11.2: Julia coupling / 12.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation;
DOI:10.1016/j.bmcl.2004.02.064

Reference yield:

: 710336-71-3
[(2S,3S)-3-((R)-1-Methyl-2-triisopropylsilanyloxy-ethyl)-oxiranyl]-methanol

: 710336-69-9
(R)-5-{(S)-6-[(1S,2R)-2-(2-Hydroxy-ethyl)-1,2-dimethyl-6-oxo-cyclohexyl]-2-methyl-4-oxo-hexyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 96 percent / DIBAL-H / toluene / 0 °C

2.1: Et₃N; DMAP / CH₂Cl₂

3.1: NaN₃ / dimethylformamide

4.1: H₂ / Pd/C / tetrahydrofuran

5.1: NaOH

6.1: 96 percent / p-TsOH / benzene

7.1: 95 percent / TBAF / tetrahydrofuran

8.1: 91 percent / n-Bu₃P; pyridine

9.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 93 h / 0 °C

10.1: n-BuLi / tetrahydrofuran / -78 °C

10.2: tetrahydrofuran

11.1: Dess-Martin periodinane; pyridine / CH₂Cl₂

12.1: 79 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

13.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

14.1: 99 percent / TBAF / tetrahydrofuran

With pyridine; methanol; dmap; sodium hydroxide; n-butyllithium; sodium azide; samarium diiodide; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 10.2: Julia coupling / 11.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1016/j.bmcl.2004.02.064