N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN

Base Information

• Chemical Name: N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN
• CAS No.: 216758-20-2
• Molecular Formula: C22H39NO5
• Molecular Weight: 397.55
• Mol file: 216758-20-2.mol

Synonyms:N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN;2R-(HYDROXYMETHYL)-1-[5-(TRICYCLO[3.3.2.13,7]DEC-1-YLMETHOXY)PENTYL]-3R,4R,5S-PIPERIDINETRIOL;ADAMANTANE-PENTYL-DNM;AMP-DEOXYNOJIRIMYCIN

Chemical Property of N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN

Chemical Property:

• Boiling Point: 569.9±50.0 °C(Predicted)
• PKA: 13.72±0.70(Predicted)
• PSA: 93.39000
• Density: 1.214±0.06 g/cm3(Predicted)
• LogP: 1.08680

Purity/Quality:

97% ^*data from raw suppliers

AMP-Deoxynojirimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A powerful inhibitor of the non-lysomal glucoceramidase at nanomolar concentrations. At these low concentrations, the lysosomal glucocerebrosidase and a-glucosidase, the glucoceramide synthetase, and the N-linked glycantrimming a-glucosidases of the endoplasmic reticulum are not affected.

Technology Process of N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN

There total 52 articles about N-(5-ADAMANTANE-1-YL-METHOXY)-PENTYL-DEOXYNOJIRIMYCIN 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: 60.0%

5-(adamantan-1-yl-methoxy)-1-bromo-pentane (850888-01-6) + 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2) → AMP-DNM (216758-20-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/jm501181z

Reference yield: 42.0%

5-(adamantan-1-yl-methoxy)-1-bromo-pentane (850888-01-6) + (2S,3R,4R,5S)-2-hydroxymethyl-3,4,5-piperidinetriol (16647-80-6) → N-[5-(adamantan-1yl-metoxy)pentyl]-L-ido-1-deoxynojirimycin (216758-20-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/jm501181z

Reference yield:

2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin (857254-45-6) → AMP-DNM (216758-20-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 20h; under 750.06 Torr;

DOI:10.1021/jo061280p

upstream raw materials:

2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

5-(adamantan-1-yl-methoxy)-1-pentanal

5-(adamantan-1-yl-methoxy)-1-pentanol

5-(adamantan-1-yl-methoxy)-1-benzyloxy-pentane

Refernces

• 1、 Ghisaidoobe, Amar T.,Van Den Berg, Richard J. B. H. N.,Butt, Saleem S.,Strijland, Anneke,Donker-Koopman, Wilma E.,Scheij, Saskia,Van Den Nieuwendijk, Adrianus M. C. H.,Koomen, Gerrit-Jan,Van Loevezijn, Arnold,Leemhuis, Mark,Wennekes, Tom,Van Der Stelt, Mario,Van Der Marel, Gijsbert A.,Van Boeckel, Constant A. A.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.. "Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors". supporting information. p. 9096 - 9104. Retrieved 2015/03/14.
• 2、 Wennekes, Tom,Meijer, Alfred J.,Groen, Albert K.,Boot, Rolf G.,Groener, Johanna E.,Van Eijk, Marco,Ottenhoff, Roelof,Bijl, Nora,Ghauharali, Karen,Song, Hang,O'Shea, Tom J.,Liu, Hanlan,Yew, Nelson,Copeland, Diane,Van Den Berg, Richard J.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Aerts, Johannes M.. "Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation". supporting information; experimental part. p. 689 - 698. Retrieved 2010/07/06.