benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate

Base Information

• Chemical Name: benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate
• CAS No.: 888616-14-6
• Molecular Formula: C₄₅H₇₁NO₁₃S
• Molecular Weight: 866.124
• Mol file: 888616-14-6.mol

Synonyms:benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate

Chemical Property of benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate

There total 6 articles about benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate 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: 80.0%

benzyl 22-carboxy-12-thiadocosanoate (888616-13-5) + N-[2-((2,3,4,6-tetra-O-acetyl)-α-D-galactopyranosyloxy)ethyl]carbamate (153324-46-0) → benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate (888616-14-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h; pH=8;

DOI:10.1039/b513944a

Reference yield:

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate (153253-02-2) → benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate (888616-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / Pd/C / ethanol / 12 h / 20 °C / 6000.48 Torr

2: 80 percent / TBTU; diisopropylethylamine / CH₂Cl₂ / 24 h / 20 °C / pH 8

With hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1039/b513944a

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → benzyl 22-[2-((2,3,4,6-tetra-O-acetyl)-β-D-galactopyranosyloxy)ethylcarbamoyl]-12-thiadocosanoate (888616-14-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / Hg(CN)2 / acetonitrile / 24 h / 20 °C

2: hydrogen / Pd/C / ethanol / 12 h / 20 °C / 6000.48 Torr

3: 80 percent / TBTU; diisopropylethylamine / CH₂Cl₂ / 24 h / 20 °C / pH 8

With hydrogen; mercury(II) cyanide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile; 1: Helferich reaction;

DOI:10.1039/b513944a

upstream raw materials:

benzyl 22-carboxy-12-thiadocosanoate

N-[2-((2,3,4,6-tetra-O-acetyl)-α-D-galactopyranosyloxy)ethyl]carbamate

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate

11-bromoundecanoic acid