(2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine

Base Information

• Chemical Name: (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine
• CAS No.: 254104-03-5
• Molecular Formula: C₂₆H₃₁NO₉S
• Molecular Weight: 533.599
• Mol file: 254104-03-5.mol

Synonyms:(2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine

Chemical Property of (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine

There total 12 articles about (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine 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: 71.0%

acetic anhydride (108-24-7) + (2R,3R)-1-tosyl-4,5-dihydroxy-2-phenylmethoxymethyl-3-piperidyl acetate (254104-00-2) → (2R,3S,4S,5S)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine (254104-01-3) + (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine (254104-03-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00382-1

Reference yield:

(furan-2-yl)ethylene (1487-18-9) → (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine (254104-03-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: K₃Fe(CN)6; (DHQD)2-PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C

2.1: KOH / 2 h / 60 °C

3.1: aq. NaN₃ / dimethylformamide / 12 h / 120 °C

4.1: NaH / dimethylformamide / 2 h / 0 °C

5.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

5.2: pyridine / 0.5 h / 0 °C

6.1: 82.4 percent / m-CPBA / CH₂Cl₂ / 20 °C

7.1: 90 percent / BF₃*Et₂O; 4A sieves / tetrahydrofuran / 4 h / 0 °C

8.1: 97.4 percent / CeCl₃; NaBH₄ / methanol / 2 h / -30 °C

9.1: 86 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

10.1: 86 percent / aq. formic acid; NaBH₄ / 4 h / 0 °C

11.1: 93 percent / K₃Fe(CN)6; (DHQD)2-PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C

12.1: 17 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; sodium azide; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Oxidation / 2.1: Carboxylation / 3.1: Decomposition / 4.1: Alkylation / 5.1: Reduction / 5.2: Tosylation / 6.1: Oxidation / 7.1: Alkylation / 8.1: Reduction / 9.1: Acetylation / 10.1: Reduction / 11.1: Oxidation / 12.1: Acetylation;

DOI:10.1016/S0957-4166(99)00382-1

Reference yield:

(S)-1-(α-furyl)-1,2-ethanediol (61243-05-8) → (2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-phenylmethoxymethyl piperidine (254104-03-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: KOH / 2 h / 60 °C

2.1: aq. NaN₃ / dimethylformamide / 12 h / 120 °C

3.1: NaH / dimethylformamide / 2 h / 0 °C

4.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

4.2: pyridine / 0.5 h / 0 °C

5.1: 82.4 percent / m-CPBA / CH₂Cl₂ / 20 °C

6.1: 90 percent / BF₃*Et₂O; 4A sieves / tetrahydrofuran / 4 h / 0 °C

7.1: 97.4 percent / CeCl₃; NaBH₄ / methanol / 2 h / -30 °C

8.1: 86 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

9.1: 86 percent / aq. formic acid; NaBH₄ / 4 h / 0 °C

10.1: 93 percent / K₃Fe(CN)6; (DHQD)2-PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 4 h / 0 °C

11.1: 17 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; sodium azide; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Carboxylation / 2.1: Decomposition / 3.1: Alkylation / 4.1: Reduction / 4.2: Tosylation / 5.1: Oxidation / 6.1: Alkylation / 7.1: Reduction / 8.1: Acetylation / 9.1: Reduction / 10.1: Oxidation / 11.1: Acetylation;

DOI:10.1016/S0957-4166(99)00382-1

upstream raw materials:

acetic anhydride

(2R,3R)-1-tosyl-4,5-dihydroxy-2-phenylmethoxymethyl-3-piperidyl acetate

(furan-2-yl)ethylene

(S)-1-(α-furyl)-1,2-ethanediol

Downstream raw materials:

(2R,3S,4R,5R)-1-tosyl-3,4,5-triacetoxy-2-hydroxymethyl piperidine

Refernces