1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol

Base Information

• Chemical Name: 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol
• CAS No.: 1346691-01-7
• Molecular Formula: C₇₂H₁₁₇O₂₃P
• Molecular Weight: 1381.68
• Mol file: 1346691-01-7.mol

Synonyms:1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol

Chemical Property of 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol

There total 8 articles about 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol 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%

3-O-benzyl-1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-DL-glycerol (1346691-00-6) + O-benzyl O-(2R)-2-hexadecanoyloxy-3-octadecanoyloxypropyl-N,N-diisopropyl phosphoramidite (228406-23-3) → 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol (1346691-01-7)

Guidance literature:

3-O-benzyl-1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-DL-glycerol; O-benzyl O-(2R)-2-hexadecanoyloxy-3-octadecanoyloxypropyl-N,N-diisopropyl phosphoramidite; In dichloromethane; acetonitrile; at 20 ℃; for 0.5h; Molecular sieve;

With 1H-tetrazole; In dichloromethane; acetonitrile; at 0 - 20 ℃; for 2h; Molecular sieve;

With magnesium sulfate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; at -40 - 20 ℃; Molecular sieve;

DOI:10.1002/cmdc.201100291

Reference yield:

2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate (1190224-19-1) → 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol (1346691-01-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere

1.2: 1 h / Inert atmosphere; Molecular sieve

1.3: 1 h / 20 °C / Inert atmosphere

2.1: acetic acid / water / 18 h

3.1: dichloromethane / 0.5 h / Molecular sieve

3.2: 1.5 h / 0 °C / Molecular sieve

4.1: dichloromethane; acetonitrile / 0.5 h / 20 °C / Molecular sieve

4.2: 2 h / 0 - 20 °C / Molecular sieve

4.3: -40 - 20 °C / Molecular sieve

With acetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1002/cmdc.201100291

Reference yield:

3-O-benzyl-2-O-hexadecanoyl-1-O-octadecanoyl-sn-glycerol (282532-76-7) → 1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-3-O-benzyl-2-O-(((S)-2-O-hexadecanoyloxy-3-O-octadecanoyloxypropyl)(benzyl)phosphoryl)-DL-glycerol (1346691-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol; dichloromethane / 4 h / 20 °C

2.1: 1H-tetrazole / dichloromethane / 0.5 h / 20 °C

3.1: dichloromethane; acetonitrile / 0.5 h / 20 °C / Molecular sieve

3.2: 2 h / 0 - 20 °C / Molecular sieve

3.3: -40 - 20 °C / Molecular sieve

With 1H-tetrazole; palladium 10% on activated carbon; hydrogen; In ethanol; dichloromethane; acetonitrile;

DOI:10.1002/cmdc.201100291

upstream raw materials:

1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-DL-glycerol

3-O-benzyl-1-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-DL-glycerol

O-benzyl O-(2R)-2-hexadecanoyloxy-3-octadecanoyloxypropyl-N,N-diisopropyl phosphoramidite

2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate

Downstream raw materials:

C₆₀H₁₀₁O₁₅P