5-acetamido-3,4-piperidinediol

Base Information

• Chemical Name: 5-acetamido-3,4-piperidinediol
• CAS No.: 111749-07-6
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• Mol file: 111749-07-6.mol

Synonyms:5-acetamido-3,4-piperidinediol

Chemical Property of 5-acetamido-3,4-piperidinediol

Chemical Property:

• Vapor Pressure: 1.8E-09mmHg at 25°C
• Boiling Point: 437°Cat760mmHg
• Flash Point: 218.1°C
• PSA: 81.59000
• Density: 1.28g/cm³
• LogP: -1.46420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-acetamido-3,4-piperidinediol

There total 5 articles about 5-acetamido-3,4-piperidinediol 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: 90.0%

(3R,4R,5S)-5-acetamido-N-benzyl-3,4-bis(benzyloxy)piperidine (111749-11-2) → (3R,4R,5S)-5-acetamido-3,4-piperidinediol (111749-07-6)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/0008-6215(87)80290-2

Reference yield:

2-acetamido-3,4-di-O-benzyl-2-deoxy-D-glucopyranoside (69892-52-0,69892-53-1,78488-34-3,78488-35-4) → (3R,4R,5S)-5-acetamido-3,4-piperidinediol (111749-07-6)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

2: LiBr / butan-2-one / 2 h / Heating

3: 53 percent / zinc, NaBH₃CN / propan-1-ol; H₂O / 3.25 h / Heating

4: 1.) trifluoroacetic acid, ozone; 2.) dimethyl sulfide, NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 5 min.; 2.) CH₂Cl₂, methanol, room temp., 20 h.

5: 90 percent / HCl, H₂ / 10percent Pd-C / ethanol

With hydrogenchloride; dimethylsulfide; hydrogen; sodium cyanoborohydride; ozone; triethylamine; trifluoroacetic acid; lithium bromide; zinc; palladium on activated charcoal; In propan-1-ol; ethanol; dichloromethane; water; butanone;

DOI:10.1016/0008-6215(87)80290-2

Reference yield:

methyl 2-acetamido-3,4-di-O-benzyl-6-bromo-2,6-dideoxy-D-glucopyranoside (111749-08-7,111749-09-8) → (3R,4R,5S)-5-acetamido-3,4-piperidinediol (111749-07-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / zinc, NaBH₃CN / propan-1-ol; H₂O / 3.25 h / Heating

2: 1.) trifluoroacetic acid, ozone; 2.) dimethyl sulfide, NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 5 min.; 2.) CH₂Cl₂, methanol, room temp., 20 h.

3: 90 percent / HCl, H₂ / 10percent Pd-C / ethanol

With hydrogenchloride; dimethylsulfide; hydrogen; sodium cyanoborohydride; ozone; trifluoroacetic acid; zinc; palladium on activated charcoal; In propan-1-ol; ethanol; water;

DOI:10.1016/0008-6215(87)80290-2

upstream raw materials:

(3R,4R,5S)-5-acetamido-N-benzyl-3,4-bis(benzyloxy)piperidine

2-acetamido-3,4-di-O-benzyl-2-deoxy-D-glucopyranoside

methyl 2-acetamido-3,4-di-O-benzyl-6-bromo-2,6-dideoxy-D-glucopyranoside

(2S,3R,4R)-2-acetamido-1-(benzylamino)-3,4-bis(benzyloxy)-hex-5-ene

Refernces