N-benzyl (+)-isofagomine

Base Information

• Chemical Name: N-benzyl (+)-isofagomine
• CAS No.: 215724-77-9
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.299
• Mol file: 215724-77-9.mol

Synonyms:N-benzyl (+)-isofagomine

Chemical Property of N-benzyl (+)-isofagomine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl (+)-isofagomine

There total 18 articles about N-benzyl (+)-isofagomine 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: 100.0%

[(3aR,7R,7aR)-5-Benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-yl]methanol (319924-34-0) → N-benzyl (+)-isofagomine (215724-77-9)

Guidance literature:

With hydrogenchloride; methanol; ammonium hydroxide; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)01553-7

Reference yield: 79.0%

benzyl chloride (100-44-7) + isofagomine (169105-89-9,275363-98-9,275363-86-5,346408-06-8,275363-99-0) → N-benzyl (+)-isofagomine (215724-77-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 14h;

Reference yield:

1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol (320396-46-1) → N-benzyl (+)-isofagomine (215724-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 660 mg / CBr₄; Ph₃P / CH₂Cl₂ / 1 h / 0 - 20 °C

2.1: 65 percent / K₂CO₃; TBAI / acetonitrile / 96 h / Heating

3.1: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation

4.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

4.2: 45 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 4 h / 0 - 20 °C

5.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C

With hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; naphthalene-1,4-dicarbonitrile; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol; acetonitrile;

DOI:10.1055/s-2001-15063

upstream raw materials:

[(3aR,7R,7aR)-5-Benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-yl]methanol

norarecoline

arecoline

methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Downstream raw materials:

isofagomine

(3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol