(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

Base Information

• Chemical Name: (2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate
• CAS No.: 879572-75-5
• Molecular Formula: C₄₁H₅₅NO₄Si
• Molecular Weight: 653.978
• Mol file: 879572-75-5.mol

Synonyms:(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

Chemical Property of (2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

There total 1 articles about (2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate 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: 98.0%

(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate (879572-72-2) → (2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate (879572-75-5)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 1h;

DOI:10.1021/ol053010j

Reference yield: 95.0%

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate (879572-75-5) → (2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-aza-spiro[4,5]decane-1-carboxylate (879572-76-6)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ol053010j

Reference yield:

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate (879572-75-5) → (2S,5S,7aS,11aS)-3-(benzyloxymethyl)decahydro-1H-pyrrolo[1,2-j]quinoline-5-carbonitrile (879572-67-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

3: 96 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

4: p-TsOH*H₂O / acetone; H₂O / 5 h / Heating

5: 9.8 mg / HCl / acetone; H₂O / 5 h / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1021/ol053010j

upstream raw materials:

(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

Downstream raw materials:

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-aza-spiro[4,5]decane-1-carboxylate

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-oxo-propyl)-1-azaspiro[4,5]decane-1-carboxylate

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-hydroxypropyl)-1-azaspiro[4,5]decane-1-carboxylate

3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline