N-dodecyldeoxynojirimycin

Base Information

• Chemical Name: N-dodecyldeoxynojirimycin
• CAS No.: 79206-22-7
• Molecular Formula: C₁₈H₃₇NO₄
• Molecular Weight: 331.496
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID20431312
• Nikkaji Number: J2.751.489H
• Wikidata: Q82245166
• Pharos Ligand ID: DB95GWXHHJRV
• ChEMBL ID: CHEMBL450985
• Mol file: 79206-22-7.mol

Synonyms:N-dodecyldeoxynojirimycin;79206-22-7;CHEMBL450985;(2R,3R,4R,5S)-1-DODECYL-2-(HYDROXYMETHYL)PIPERIDINE-3,4,5-TRIOL;N-DODECYL-1-DEOXYNOJIRIMYCIN;DTXSID20431312;BDBM50242628;N-Dodecyl-1-deoxynojirimycin, >=98.0% (TLC);W-203810;(2R,3R,4R,5S)-1-Dodecyl-2-(hydroxymethyl)-3,4,5-piperidinetriol

Chemical Property of N-dodecyldeoxynojirimycin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-102°C
• Refractive Index: 1.514
• Boiling Point: 486.916°C at 760 mmHg
• Flash Point: 233.788°C
• PSA: 84.16000
• Density: 1.07g/cm³
• LogP: 2.40640
• Storage Temp.: -20°C Freezer
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 331.27225866
• Heavy Atom Count: 23
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

N-Dodecyldeoxynojirimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCN1CC(C(C(C1CO)O)O)O
• Isomeric SMILES: CCCCCCCCCCCCN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
• Uses: Affects trimming glucosidases to a lesser degree than Deoxynojirimycin or N-Methyl- deoxynojirimycin Affects trimming glucosidases to a lesser degree than Deoxynojirimycin or N-Methyl- deoxynojirimycin.

Technology Process of N-dodecyldeoxynojirimycin

There total 3 articles about N-dodecyldeoxynojirimycin 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: 27.0%

n-Dodecylamine (124-22-1) + D-xylo-hexos-5-ulose (19684-22-1) → N-Dodecyl-1-deoxynojirimycin (79206-22-7)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; 1.) -78 deg C, 2 h, 2.) r.t., 66 h;

DOI:10.1021/jo00090a040

Reference yield:

1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose (19684-32-3) → N-Dodecyl-1-deoxynojirimycin (79206-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Dowex 50W-X₈ / H₂O / 36 h / 25 °C

2: 27 percent / HOAc, NaBH₃CN / methanol / 1.) -78 deg C, 2 h, 2.) r.t., 66 h

With Dowex 50W-X₈; sodium cyanoborohydride; acetic acid; In methanol; water;

DOI:10.1021/jo00090a040

Reference yield:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → N-Dodecyl-1-deoxynojirimycin (79206-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutylin oxide hemihydrate, 2.) Br₂ / 1.) MeOH, reflux, 1.5 h, 2.) CH₂Cl₂, 0 deg C, 10 min

2: 70 percent / Dowex 50W-X₈ / H₂O / 36 h / 25 °C

3: 27 percent / HOAc, NaBH₃CN / methanol / 1.) -78 deg C, 2 h, 2.) r.t., 66 h

With Dowex 50W-X₈; bromine; di(n-butyl)tin oxide; sodium cyanoborohydride; acetic acid; In methanol; water;

DOI:10.1021/jo00090a040

upstream raw materials:

n-Dodecylamine

D-xylo-hexos-5-ulose

1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose

1,2-O-isopropylidene-α-D-glucofuranose

Refernces