(1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

Base Information

• Chemical Name: (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one
• CAS No.: 253882-56-3
• Molecular Formula: C₃₃H₄₇NO₅SSi
• Molecular Weight: 597.891
• Mol file: 253882-56-3.mol

Synonyms:(1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

Chemical Property of (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

There total 13 articles about (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one 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: 70.0%

(R)-7-Benzyloxy-4-[(R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid methyl ester (253882-55-2) → (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one (253882-56-3) + (R)-7-Benzyloxy-4-[(R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid

Guidance literature:

With lithium n-propylmercaptide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃;

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

Reference yield:

di(p-tolyl) disulfide (103-19-5) → (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one (253882-56-3)

Guidance literature:

Multi-step reaction with 10 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: 70 percent / PrSLi / hexamethylphosphoric acid triamide / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; tributylphosphine; lithium n-propylmercaptide; Dess-Martin periodane; dimedone; 4-methylmorpholine N-oxide; trifluoroacetic acid; calcium chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetone; 1: Substitution / 2: Oxidation / 3: Hydrolysis / 4: Acylation / 5: Reduction / 6: Etherification / 7: Addition / 8: Oxidation / 9: Cyclization / 10: Cyclization;

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

Reference yield:

(R)-7-Benzyloxy-4-formyl-heptanoic acid methyl ester (253882-52-9) → (1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one (253882-56-3)

Guidance literature:

Multi-step reaction with 4 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: 70 percent / PrSLi / hexamethylphosphoric acid triamide / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; lithium n-propylmercaptide; Dess-Martin periodane; dimedone; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1: Addition / 2: Oxidation / 3: Cyclization / 4: Cyclization;

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

upstream raw materials:

(R)-7-Benzyloxy-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

Downstream raw materials:

(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(3-hydroxy-propyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

(1S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(3-iodo-propyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one