1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane

Base Information

• Chemical Name: 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane
• CAS No.: 134179-46-7
• Molecular Formula: C₄₄H₅₈N₂O₈
• Molecular Weight: 742.953
• Mol file: 134179-46-7.mol

Synonyms:1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane

Chemical Property of 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane

There total 6 articles about 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane 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: 89.0%

1-azido-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane → 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane (134179-46-7)

Guidance literature:

With 1.3-propanedithiol; triethylamine; In methanol; for 48h; Ambient temperature;

DOI:10.1021/jo00013a053

Reference yield:

Tetraethylene glycol (112-60-7) → 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane (134179-46-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) NaH / 1) THF, mineral oil, 0 deg C, 2) THF, 30 min at r.t.

2: Et₃N / 3 h / Ambient temperature

3: 73 percent / NaN₃ / aq. ethanol / 8 h / Heating

4: 80 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

5: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 75 percent / 1,2-dimethoxy-ethane / 0.5 h / Heating

7: 1) 55percent hydrazine hydrate, 2) conc. HCl / 1) MeOH, 2 h, reflux, 2) water, 1 h, reflux

8: 1) methanolic HCl, 2) sodium cyanoborohydride / 1) MeOH, 10 min, 2) 24 h, r.t.

9: 89 percent / Et₃N, 1,3-propanedithiol / methanol / 48 h / Ambient temperature

With 1.3-propanedithiol; hydrogenchloride; sodium azide; tetrabutyl ammonium fluoride; sodium hydride; sodium cyanoborohydride; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane;

DOI:10.1021/jo00013a053

Reference yield:

2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol (86770-67-4) → 1-amino-11-<<2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl>amino>-3,6,9-trioxaundecane (134179-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 75 percent / 1,2-dimethoxy-ethane / 0.5 h / Heating

3: 1) 55percent hydrazine hydrate, 2) conc. HCl / 1) MeOH, 2 h, reflux, 2) water, 1 h, reflux

4: 1) methanolic HCl, 2) sodium cyanoborohydride / 1) MeOH, 10 min, 2) 24 h, r.t.

5: 89 percent / Et₃N, 1,3-propanedithiol / methanol / 48 h / Ambient temperature

With 1.3-propanedithiol; hydrogenchloride; sodium cyanoborohydride; hydrazine hydrate; triethylamine; In methanol; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jo00013a053

upstream raw materials:

Tetraethylene glycol

2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol

2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine

11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane

Downstream raw materials:

2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-5-(3-{2-[2-(2-{2-[2-((2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-thioureido)-benzoic acid

Refernces