t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate

Base Information

• Chemical Name: t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate
• CAS No.: 864070-79-1
• Molecular Formula: C₃₅H₃₇NO₁₂S
• Molecular Weight: 695.744
• Mol file: 864070-79-1.mol

Synonyms:t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate

Chemical Property of t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate

There total 5 articles about t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate 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: 81.0%

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate (864070-76-8) + diazomethyl-trimethyl-silane (18107-18-1) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate (864070-79-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; acetonitrile; at 5 ℃; for 20h;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-74-6) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate (864070-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / pyridine / 25 h

2: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / 0 °C

3: 81 percent / diisopropylethylamine / methanol; acetonitrile / 20 h / 5 °C

With pyridine; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-75-7) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6'-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate (864070-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / 0 °C

2: 81 percent / diisopropylethylamine / methanol; acetonitrile / 20 h / 5 °C

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

diazomethyl-trimethyl-silane

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate

Downstream raw materials:

t-butyl (Z)-2-(2'-deoxy-2'-[4-benzoylphenyl]methylamino-6'-[N-(N-(N-(biotinyl)glycyl)glycyl)glycyl]-amino-6'-deoxy-β-D-galactopyranosyloxy)-3-p-methoxyphenyl-2-acrylate