(3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one

Base Information

• Chemical Name: (3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one
• CAS No.: 156857-10-2
• Molecular Formula: C₆H₁₁NO₅
• Molecular Weight: 177.157
• Mol file: 156857-10-2.mol

Synonyms:2-Piperidinone,3,4,5-trihydroxy-6-(hydroxymethyl)-, (3a,4a,5b,6a)- (9CI); 2-Piperidinone,3,4,5-trihydroxy-6-(hydroxymethyl)-, (3a,4a,5b,6a)-(?à)-

Chemical Property of (3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one

Chemical Property:

• Vapor Pressure: 4.03E-12mmHg at 25°C
• Boiling Point: 500.6°Cat760mmHg
• PKA: 11.88±0.70(Predicted)
• Flash Point: 256.6°C
• PSA: 113.51000
• Density: 1.632g/cm³
• LogP: -3.16430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one

There total 129 articles about (3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one 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: 80.0%

ethyl (2R,3R,4R,5R)-5-azido-4,6-bis(benzyloxy)-2,3-dihydroxyhexanoate (1427467-87-5) → nojirimycin-δ-lactam (14904-83-7,156857-10-2)

Guidance literature:

ethyl (2R,3R,4R,5R)-5-azido-4,6-bis(benzyloxy)-2,3-dihydroxyhexanoate; With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 48h;

With water;

DOI:10.3998/ark.5550190.0013.925

Reference yield: 77.0%

2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam (294204-04-9) → nojirimycin-δ-lactam (14904-83-7,156857-10-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 6h;

DOI:10.1021/jo000141j

Reference yield: 57.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4) → nojirimycin-δ-lactam (14904-83-7,156857-10-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium dihydroxide; palladium on activated charcoal; In methanol; ethanol; for 48h;

DOI:10.1016/S0040-4020(01)86715-6

upstream raw materials:

nojirimycin

nojirimycin

(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

5-Amino-5-deoxy-3,6-di-O-benzyl-D-glucono-δ-lactam