ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside
• CAS No.: 254444-74-1
• Molecular Formula: C₃₄H₄₁NO₁₇S
• Molecular Weight: 767.762
• Mol file: 254444-74-1.mol

Synonyms:ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside

Chemical Property of ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside

There total 1 articles about ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside 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: 86.0%

phthalic anhydride (85-44-9) + C26H39NO15S*ClH (1622250-75-2) → ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside (254444-74-1)

Guidance literature:

With pyridine; acetic anhydride; triethylamine; at 95 ℃;

DOI:10.1039/c4sc01013b

Reference yield: 80.0%

2-azidoethyl (2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1→6)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)]-(3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside + ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside (254444-74-1) → 2-azidoethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1→6)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)]-(3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -25 - -10 ℃; for 0.75h; Molecular sieve;

DOI:10.1007/s11172-014-0462-5

Reference yield:

ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside (254444-74-1) → Ethyl 6-O-benzoyl-3-O-chloroacetyl-4-O-(2,6-di-O-benzoyl-3:4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / K₂CO₃; MeOH / tetrahydrofuran / 0.67 h

2.1: 88 percent / p-TsOH / dimethylsulfoxide / 12 h

3.1: 86 percent / NEt₃ / tetrahydrofuran / 22 h / -80 - -45 °C

4.1: dibutyltin dimethoxide / toluene / 1.5 h / Heating

4.2: 98 percent / molecular sieves 4 Angstrfoem / toluene / 3 h

5.1: 90 percent / pyridine / CH₂Cl₂ / 12 h

With pyridine; methanol; dibutyldimethoxytin; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Deacetylation / 2.1: Etherification / 3.1: Esterification / 4.1: Metallation / 4.2: Esterification / 5.1: Esterification;

upstream raw materials:

phthalic anhydride

C₂₆H₃₉NO₁₅S*ClH

Downstream raw materials:

Ethyl 6-O-benzoyl-4-O-(6-O-benzoyl-3:4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

Ethyl 6-O-benzoyl-4-O-(2,6-di-O-benzoyl-3:4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

C₅₁H₆₀Cl₃NO₂₄S

5-benzyloxycarbonylamino-1-pentyl(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1→2)-[4,6-di-O-acetyl-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranosyl]-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-β-D-glucopyranoside