(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:213964-78-4
Molecular Formula:C₃₂H₄₇NO₈
Molecular Weight:573.727
Hs Code.:

(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Synonyms:(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of (R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 28 articles about (R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl 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:

: 53558-93-3
(R)-tetrahydro-5-oxo-2-furancarboxylic acid

: 213964-78-4
(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: BH₃*SMe₂ / tetrahydrofuran

2: imidazole / dimethylformamide

3: LDA / tetrahydrofuran / -78 °C

4: TBAF / tetrahydrofuran / 1 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: NaN₃ / dimethylformamide / 2 h / 90 °C

7: H₂ / Pd/C / tetrahydrofuran / 2 h / Ambient temperature

8: Et₃N / tetrahydrofuran

9: 94 percent / NaBH₄ / methanol; tetrahydrofuran / 0.25 h / 60 °C

10: 74 percent / n-Bu₃P / pyridine / 1 h / Ambient temperature

11: p-TsOH / acetone / 1 h / Ambient temperature

12: MCPBA, NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

13: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

14: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

15: 87 percent / Na-Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

16: TBAF / tetrahydrofuran / 18 h / Ambient temperature

17: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

18: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

With 1H-imidazole; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium azide; sodium amalgam; 2-methyl-but-2-ene; tributylphosphine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01284-2

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 213964-78-4
(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: imidazole / dimethylformamide

2: LDA / tetrahydrofuran / -78 °C

3: TBAF / tetrahydrofuran / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: NaN₃ / dimethylformamide / 2 h / 90 °C

6: H₂ / Pd/C / tetrahydrofuran / 2 h / Ambient temperature

7: Et₃N / tetrahydrofuran

8: 94 percent / NaBH₄ / methanol; tetrahydrofuran / 0.25 h / 60 °C

9: 74 percent / n-Bu₃P / pyridine / 1 h / Ambient temperature

10: p-TsOH / acetone / 1 h / Ambient temperature

11: MCPBA, NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

12: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

13: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

14: 87 percent / Na-Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

15: TBAF / tetrahydrofuran / 18 h / Ambient temperature

16: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

17: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

With 1H-imidazole; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium azide; sodium amalgam; 2-methyl-but-2-ene; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01284-2

Reference yield:

: 6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
D-Glutamic acid

: 213964-78-4
(R)-5-[(S)-6-((6S,7R)-7-Carboxymethyl-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-2-methyl-4-oxo-hexyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: NaNO₂ / H₂O

2: BH₃*SMe₂ / tetrahydrofuran

3: imidazole / dimethylformamide

4: LDA / tetrahydrofuran / -78 °C

5: TBAF / tetrahydrofuran / 1 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

7: NaN₃ / dimethylformamide / 2 h / 90 °C

8: H₂ / Pd/C / tetrahydrofuran / 2 h / Ambient temperature

9: Et₃N / tetrahydrofuran

10: 94 percent / NaBH₄ / methanol; tetrahydrofuran / 0.25 h / 60 °C

11: 74 percent / n-Bu₃P / pyridine / 1 h / Ambient temperature

12: p-TsOH / acetone / 1 h / Ambient temperature

13: MCPBA, NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

14: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

15: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

16: 87 percent / Na-Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

17: TBAF / tetrahydrofuran / 18 h / Ambient temperature

18: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

19: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

With 1H-imidazole; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium azide; sodium amalgam; 2-methyl-but-2-ene; tributylphosphine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01284-2