3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester

Base Information

• Chemical Name: 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester
• CAS No.: 253882-62-1
• Molecular Formula: C₂₇H₄₅NO₅SSi
• Molecular Weight: 523.81
• Mol file: 253882-62-1.mol

Synonyms:3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester

Chemical Property of 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester

There total 15 articles about 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl 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: 57.0%

(S)-7-Bromo-4-[(R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid methyl ester (253882-61-0) → (R)-4-[(R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid methyl ester + 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester (253882-62-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 75 ℃; for 5h;

DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

di(p-tolyl) disulfide (103-19-5) → 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester (253882-62-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / Bu₃P / CH₂Cl₂ / 3 h

2: 91 percent / OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 8 h

3: CF₃COOH; Me₂S / CH₂Cl₂ / 3 h

4: pyridine / 0.5 h / 0 °C

5: NaBH₄; CaCl₂ / tetrahydrofuran; ethanol

6: imdazole / tetrahydrofuran / 3 h

7: 77 percent / BuLi / tetrahydrofuran / 0.75 h / -78 °C

8: 90 percent / Dess-Martin reagent / CH₂Cl₂

9: 88 percent / (Ph₃P)4Pd; dimedone / tetrahydrofuran / 2 h

10: 90 percent / H₂ / Pd-C / ethyl acetate; methanol

11: 82 percent / Ph₃P; 2,6-lutidine; CBr₄ / acetonitrile / 0.5 h / 0 °C

12: 57 percent / Bu₃SnH; AIBN / toluene / 5 h / 75 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; hydrogen; tri-n-butyl-tin hydride; Dess-Martin periodane; dimedone; 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; 1: Substitution / 2: Oxidation / 3: Hydrolysis / 4: Acylation / 5: Reduction / 6: Etherification / 7: Addition / 8: Oxidation / 9: Cyclization / 10: Hydrogenolysis / 11: Bromination / 12: Cyclization;

DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

(R)-7-Benzyloxy-4-formyl-heptanoic acid methyl ester (253882-52-9) → 3-[(1R,5R,7R,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-10-(toluene-4-sulfonyl)-6-aza-spiro[4.5]dec-1-yl]-propionic acid methyl ester (253882-62-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / BuLi / tetrahydrofuran / 0.75 h / -78 °C

2: 90 percent / Dess-Martin reagent / CH₂Cl₂

3: 88 percent / (Ph₃P)4Pd; dimedone / tetrahydrofuran / 2 h

4: 90 percent / H₂ / Pd-C / ethyl acetate; methanol

5: 82 percent / Ph₃P; 2,6-lutidine; CBr₄ / acetonitrile / 0.5 h / 0 °C

6: 57 percent / Bu₃SnH; AIBN / toluene / 5 h / 75 °C

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; hydrogen; tri-n-butyl-tin hydride; Dess-Martin periodane; dimedone; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 1: Addition / 2: Oxidation / 3: Cyclization / 4: Hydrogenolysis / 5: Bromination / 6: Cyclization;

DOI:10.1016/S0040-4039(99)01815-8

upstream raw materials:

(S)-7-Bromo-4-[(R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid methyl ester

di(p-tolyl) disulfide

(R)-7-Benzyloxy-4-formyl-heptanoic acid methyl ester

(R)-2-Amino-5-(toluene-4-sulfonyl)-pentanoic acid methyl ester