(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

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Chemical Name:(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
CAS No.:253882-61-0
Molecular Formula:C₂₇H₄₄BrNO₅SSi
Molecular Weight:602.706
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 14 articles about (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 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: 82.0%

: 253882-60-9
(R)-4-[(R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-7-hydroxy-heptanoic acid methyl ester

: 253882-61-0
(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

Guidance literature:: With 2,6-dimethylpyridine; carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

: 103-19-5
di(p-tolyl) disulfide

: 253882-61-0
(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

Guidance literature:: Multi-step reaction with 11 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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; carbon tetrabromide; tributylphosphine; hydrogen; 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; acetonitrile; 1: Substitution / 2: Oxidation / 3: Hydrolysis / 4: Acylation / 5: Reduction / 6: Etherification / 7: Addition / 8: Oxidation / 9: Cyclization / 10: Hydrogenolysis / 11: Bromination;
DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

: 253882-43-8
(R)-2-Amino-5-(toluene-4-sulfonyl)-pentanoic acid methyl ester

: 253882-61-0
(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

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 0.5 h / 0 °C

2: NaBH₄; CaCl₂ / tetrahydrofuran; ethanol

3: imdazole / tetrahydrofuran / 3 h

4: 77 percent / BuLi / tetrahydrofuran / 0.75 h / -78 °C

5: 90 percent / Dess-Martin reagent / CH₂Cl₂

6: 88 percent / (Ph₃P)4Pd; dimedone / tetrahydrofuran / 2 h

7: 90 percent / H₂ / Pd-C / ethyl acetate; methanol

8: 82 percent / Ph₃P; 2,6-lutidine; CBr₄ / acetonitrile / 0.5 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; carbon tetrabromide; hydrogen; Dess-Martin periodane; dimedone; triphenylphosphine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetonitrile; 1: Acylation / 2: Reduction / 3: Etherification / 4: Addition / 5: Oxidation / 6: Cyclization / 7: Hydrogenolysis / 8: Bromination;
DOI:10.1016/S0040-4039(99)01815-8