(2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol
• CAS No.: 243663-16-3
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• Mol file: 243663-16-3.mol

Synonyms:

Chemical Property of (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol

There total 5 articles about (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol 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:

(4S,5S,2E)-5-amino-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-hexen-1,4-diol (194146-32-2) → (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol (243663-16-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / 4-(dimethylamino)pyridine; pyridine / 48 h

2.1: K₃Fe(CN)6; K₂CO₃; CH₃SO₂NH₂ / K₂OsO₂(OH)4 / H₂O; 2-methyl-propan-2-ol / 20 °C

2.2: 50 percent / Na₂SO₃ / 2-methyl-propan-2-ol; H₂O / 0.33 h

3.1: 90 percent / nBu₄NF / tetrahydrofuran / 3 h / 20 °C

4.1: 2,2,6,6-tetramethylpiperidine-N-oxide; NaOCl; NaHCO₃ / KBr; tetrabutylammonium chloride hydrate / CH₂Cl₂; H₂O

5.1: glacial acetic acid; NaBH₃CN / acetonitrile / 0.17 h / pH 5 - 6

6.1: 85 percent / nBu₄NOH / dioxane; H₂O

With pyridine; dmap; sodium hypochlorite; TEMPO; methanesulfonamide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); tetrabutyl-ammonium chloride; potassium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Acylation / 2.1: osmylation / 2.2: Hydrolysis / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Cyclization / 6.1: Hydrolysis;

DOI:10.1021/jo9820115

Reference yield:

(4S,5S,2E)-5-amino-1-O-tert-butyldimethylsilyl-N-diphenylmethylene-4-O-pivaloyl-2-hexen-1,4-diol (194146-46-8) → (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol (243663-16-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₃Fe(CN)6; K₂CO₃; CH₃SO₂NH₂ / K₂OsO₂(OH)4 / H₂O; 2-methyl-propan-2-ol / 20 °C

1.2: 50 percent / Na₂SO₃ / 2-methyl-propan-2-ol; H₂O / 0.33 h

2.1: 90 percent / nBu₄NF / tetrahydrofuran / 3 h / 20 °C

3.1: 2,2,6,6-tetramethylpiperidine-N-oxide; NaOCl; NaHCO₃ / KBr; tetrabutylammonium chloride hydrate / CH₂Cl₂; H₂O

4.1: glacial acetic acid; NaBH₃CN / acetonitrile / 0.17 h / pH 5 - 6

5.1: 85 percent / nBu₄NOH / dioxane; H₂O

With sodium hypochlorite; TEMPO; methanesulfonamide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); tetrabutyl-ammonium chloride; potassium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: osmylation / 1.2: Hydrolysis / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Cyclization / 5.1: Hydrolysis;

DOI:10.1021/jo9820115

Reference yield:

5-amino-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol (194146-54-8) → (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol (243663-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,6,6-tetramethylpiperidine-N-oxide; NaOCl; NaHCO₃ / KBr; tetrabutylammonium chloride hydrate / CH₂Cl₂; H₂O

2: glacial acetic acid; NaBH₃CN / acetonitrile / 0.17 h / pH 5 - 6

3: 85 percent / nBu₄NOH / dioxane; H₂O

With sodium hypochlorite; TEMPO; tetra(n-butyl)ammonium hydroxide; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; tetrabutyl-ammonium chloride; potassium bromide; In 1,4-dioxane; dichloromethane; water; acetonitrile; 1: Oxidation / 2: Cyclization / 3: Hydrolysis;

DOI:10.1021/jo9820115

upstream raw materials:

(4S,5S,2E)-5-amino-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-hexen-1,4-diol

(2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al

5-amino-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol

(4S,5S,2E)-5-amino-1-O-tert-butyldimethylsilyl-N-diphenylmethylene-4-O-pivaloyl-2-hexen-1,4-diol

Downstream raw materials:

deoxyfuconojirimycin

1,5-Didesoxy-1,5-imino-N-methyl-L-fucit

Refernces