(R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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.: 213964-91-1
• Molecular Formula: C₄₄H₆₇NO₉SSi
• Molecular Weight: 814.169
• Mol file: 213964-91-1.mol

Synonyms:(R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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

Chemical Property of (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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 26 articles about (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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:

(R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl}-4-hydroxy-2-methyl-hexyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (213964-90-0) → (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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 (213964-91-1)

Guidance literature:

With Dess-Martin periodane; In pyridine; dichloromethane; for 2h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)01284-2

Reference yield:

(R)-tetrahydro-5-oxo-2-furancarboxylic acid (53558-93-3) → (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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 (213964-91-1)

Guidance literature:

Multi-step reaction with 14 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

With 1H-imidazole; sodium tetrahydroborate; sodium azide; 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; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(98)01284-2

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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 (213964-91-1)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; sodium tetrahydroborate; sodium azide; 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; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(98)01284-2

upstream raw materials:

(R)-5-((S)-3-Benzenesulfonyl-6-{(6S,7R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,7-dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl}-4-hydroxy-2-methyl-hexyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

3-((6S,7R)-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl)propanal

(R)-5-((S)-3-Benzenesulfonyl-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(R)-tetrahydro-5-oxo-2-furancarboxylic acid

Downstream raw materials:

(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

(R)-5-((S)-6-{(6S,7R)-7-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-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