[10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester

Base Information

• Chemical Name: [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester
• CAS No.: 893421-28-8
• Molecular Formula: C₄₈H₆₅O₈PS
• Molecular Weight: 833.079
• Mol file: 893421-28-8.mol

Synonyms:[10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester

Chemical Property of [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester

There total 3 articles about [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester 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: 28.0%

10-diethoxyphosphoryl-1-O-tosyldecanol + 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose (405060-39-1) → [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester (893421-28-8)

Guidance literature:

2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose; With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

10-diethoxyphosphoryl-1-O-tosyldecanol; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2006.03.024

Reference yield:

bis[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl]disulfide (893421-26-6) → [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester (893421-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₃P / tetrahydrofuran / 3 h / 20 °C

2.1: Cs₂CO₃ / dimethylformamide / 0.17 h / 20 °C

2.2: 28 percent / dimethylformamide / 3 h / 20 °C

With tributylphosphine; caesium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.03.024

Reference yield:

1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside (405060-38-0) → [10-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-decyl]-phosphonic acid diethyl ester (893421-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MeONa / tetrahydrofuran; methanol / 1 h

2.1: Cs₂CO₃ / dimethylformamide / 0.17 h / 20 °C

2.2: 28 percent / dimethylformamide / 3 h / 20 °C

With sodium methylate; caesium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.03.024

upstream raw materials:

2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose

bis[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl]disulfide

1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside