5-amino-5-deoxygluconic acid delta-lactam

Base Information

• Chemical Name: 5-amino-5-deoxygluconic acid delta-lactam
• CAS No.: 14904-83-7
• Molecular Formula: C₆H₁₁NO₅
• Molecular Weight: 177.157
• Hs Code.: 2933790090
• Mol file: 14904-83-7.mol

Synonyms:2-Piperidinone,3,4,5-trihydroxy-6-(hydroxymethyl)-, [3R-(3a,4b,5a,6b)]-; 5-Amino-5-deoxy-D-gluconic acid d-lactam; D-Gluconic-d-lactam; D-Glucono-1,5-lactam;D-Glucono-D-lactam; d-Gluconolactam

Chemical Property of 5-amino-5-deoxygluconic acid delta-lactam

Chemical Property:

• Vapor Pressure: 4.03E-12mmHg at 25°C
• Refractive Index: 1.608
• Boiling Point: 500.6°C at 760 mmHg
• 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 5-amino-5-deoxygluconic acid delta-lactam

There total 29 articles about 5-amino-5-deoxygluconic acid delta-lactam 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

Refernces

• 1、 Ravinder, Mettu,Reddy, Thatikonda Narendar,Mahendar, Budde,Rao, Vaidya Jayathirtha. "Stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam from a common chiral intermediate derived from D-mannitol". . p. 287 - 302. Retrieved 2013/02/26.
• 2、 Nishimura, Yoshio,Adachi, Hayamitsu,Satoh, Takahiko,Shitara, Eiki,Nakamura, Hikaru,Kojima, Fukiko,Takeuchi, Tomio. "All eight stereoisomeric D-glyconic-δ-lactams: Synthesis, conformational analysis, and evaluation as glycosidase inhibitors". . p. 4871 - 4882. Retrieved 2007/10/03.