1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol

Base Information

• Chemical Name: 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol
• CAS No.: 164989-47-3
• Molecular Formula: C₇₆H₁₁₉NO₇
• Molecular Weight: 1158.78
• Mol file: 164989-47-3.mol

Synonyms:1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol

Chemical Property of 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol

There total 13 articles about 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol 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:

2-hexadecyloxirane (7390-81-0) → 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol (164989-47-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 60 percent / aq. H₂SO₄ / 2-methyl-propan-2-ol / 16 h / Heating

2: 91 percent / pyridine / CH₂Cl₂ / 16 h / 30 °C

3: 91 percent / pyridine / 1.5 h / 0 - 20 °C

4: 98 percent / NaN₃ / dimethylformamide / 16 h / 100 °C

5: 93 percent / HCl(gas) / methanol; CH₂Cl₂ / 3 h / Ambient temperature

6: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, from -10 deg C to RT, 2 h

7: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

8: WSC-HCl / CH₂Cl₂ / 1 h / Heating

With pyridine; hydrogenchloride; sodium azide; 4 A molecular sieve; sulfuric acid; hydrogen; silver perchlorate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00012a018

Reference yield:

rac-1,2-dihydroxyoctadecane (20294-76-2) → 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol (164989-47-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / pyridine / CH₂Cl₂ / 16 h / 30 °C

2: 91 percent / pyridine / 1.5 h / 0 - 20 °C

3: 98 percent / NaN₃ / dimethylformamide / 16 h / 100 °C

4: 93 percent / HCl(gas) / methanol; CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, from -10 deg C to RT, 2 h

6: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

7: WSC-HCl / CH₂Cl₂ / 1 h / Heating

With pyridine; hydrogenchloride; sodium azide; 4 A molecular sieve; hydrogen; silver perchlorate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00012a018

Reference yield:

1-bromo-hexane (111-25-1) → 1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)octadecanol (164989-47-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 12 h / 150 °C

2: 1.) nBuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, RT, 16 h

3: 88 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h

4: 93 percent / HCl(gas) / methanol; CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, from -10 deg C to RT, 2 h

6: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

7: WSC-HCl / CH₂Cl₂ / 1 h / Heating

With hydrogenchloride; n-butyllithium; 4 A molecular sieve; hydrogen; silver perchlorate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00012a018

upstream raw materials:

n-tetracosanoic acid

1-((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecylamine

2-hexadecyloxirane

rac-1,2-dihydroxyoctadecane

Refernces