methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate

Base Information

• Chemical Name: methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate
• CAS No.: 140484-45-3
• Molecular Formula: C₃₅H₄₃NO₁₄S
• Molecular Weight: 733.791
• Mol file: 140484-45-3.mol

Synonyms:methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate

Chemical Property of methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate

There total 4 articles about methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate 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: 67.0%

2-Benzyloxyethanol (622-08-2,1201808-31-2) + methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate (120123-59-3) → methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate (140484-45-3)

Guidance literature:

With disodium hydrogenphosphate; 4 A molecular sieve; silver trifluoromethanesulfonate; for 15h; Ambient temperature;

DOI:10.1016/0008-6215(92)84099-E

Reference yield: 52.0%

2-Benzyloxyethanol (622-08-2,1201808-31-2) + methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate (140484-48-6) → methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate (140484-45-3)

Guidance literature:

With disodium hydrogenphosphate; 4 A molecular sieve; silver trifluoromethanesulfonate; for 15h; Ambient temperature;

DOI:10.1016/0008-6215(92)84099-E

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate (120123-59-3) → methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L-gluco-2-nonulopyranosid>onate (140484-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Hg(CN)2, HgBr₂ / 1,2-dichloro-ethane; H₂O / 4 h / 70 °C

2: 0.66 g / CBr₄, hexamethylphosphoric triamide (HMPT) / tetrahydrofuran / 10 h / Ambient temperature

3: 52 percent / Na₂HPO₄, 4A molecular sieves, AgOSO₂CF₃ / 15 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; carbon tetrabromide; 4 A molecular sieve; silver trifluoromethanesulfonate; mercury(II) cyanide; mercury dibromide; In tetrahydrofuran; water; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(92)84099-E

upstream raw materials:

2-Benzyloxyethanol

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosonate

Downstream raw materials:

methyl <2-(benzyloxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid>onate