(2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane

Base Information

• Chemical Name: (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane
• CAS No.: 321734-90-1
• Molecular Formula: C₈₈H₁₂₇NO₉
• Molecular Weight: 1342.98

Synonyms:(2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane

Chemical Property of (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane

There total 4 articles about (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane 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: 90.0%

n-docosanoic acid (112-85-6) + (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (321734-88-7) → (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane (321734-90-1)

Guidance literature:

(2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

n-docosanoic acid; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(00)00366-9

Reference yield:

Methanesulfonic acid (E)-(1R,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-5-enyl ester → (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane (321734-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / tosylhydrazide; aq. NaOAc / ethanol / 5 h / Heating

2.1: 84 percent / NaN₃ / dimethylsulfoxide / 36 h / 100 °C

3.1: 80 percent / H₂ / 5 percent Pd/CaCO₃ / ethanol; ethyl acetate / 12 h / 760 Torr

4.1: EDAC; HOBt / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

4.2: 90 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

With sodium azide; hydrogen; sodium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; toluene-4-sulfonic acid hydrazide; Lindlar's catalyst; In ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Substitution / 3.1: Hydrogenation / 4.1: activation / 4.2: Acylation;

DOI:10.1016/S0957-4166(00)00366-9

Reference yield:

(2S,3R,4S,5S,6R)-2-((2S,3R,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran (321735-10-8) → (2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane (321734-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / H₂ / 5 percent Pd/CaCO₃ / ethanol; ethyl acetate / 12 h / 760 Torr

2.1: EDAC; HOBt / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

2.2: 90 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Lindlar's catalyst; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Hydrogenation / 2.1: activation / 2.2: Acylation;

DOI:10.1016/S0957-4166(00)00366-9

upstream raw materials:

n-docosanoic acid

(2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

(2S,3R,4S,5S,6R)-2-((2S,3R,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Methanesulfonic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl ester

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