tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate
• CAS No.: 1393105-96-8
• Molecular Formula: C₃₄H₄₅NO₆Si
• Molecular Weight: 591.82

Synonyms:tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Chemical Property of tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

There total 8 articles about tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-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:

tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-(tert-butyldiphenylsilyloxy)pyridine-1(2H)-carboxylate (1393105-94-6) → tert-butyl 2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate (1393105-98-0) + tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate (1393105-96-8)

Guidance literature:

With potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; at -10 ℃; for 48h; Inert atmosphere;

DOI:10.1002/ejoc.201200377

Reference yield:

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-30-7) → tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate (1393105-96-8)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux; Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / -75 °C / Inert atmosphere

5: water; sodium hydroxide / methanol / 3 h / 0 - 20 °C / Inert atmosphere

6: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7: potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / -10 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; potassium osmate(VI) dihydrate; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1002/ejoc.201200377

Reference yield:

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate (1241959-31-8) → tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate (1393105-96-8)

Guidance literature:

Multi-step reaction with 6 steps

1: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux; Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / -75 °C / Inert atmosphere

4: water; sodium hydroxide / methanol / 3 h / 0 - 20 °C / Inert atmosphere

5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

6: potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / -10 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; potassium osmate(VI) dihydrate; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu reaction;

DOI:10.1002/ejoc.201200377

upstream raw materials:

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate

tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Downstream raw materials:

tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

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