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

Base Information

• Chemical Name: t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate
• CAS No.: 864070-75-7
• Molecular Formula: C₄₀H₄₉NO₁₂SSi
• Molecular Weight: 795.98
• Mol file: 864070-75-7.mol

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

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

There total 3 articles about t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-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: 45.0%

t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-74-6) + p-toluenesulfonyl chloride (98-59-9) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-75-7)

Guidance literature:

With pyridine; for 25h;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (544703-53-9) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / sodium methoxide / methanol / 1 h / -30 °C

2: 45 percent / pyridine / 25 h

With pyridine; sodium methylate; In methanol;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate (544703-52-8) → t-butyl (Z)-2-(2'-deoxy-2'-phthalimido-6-O-p-toluenesulfonyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate (864070-75-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 490 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 48 h / Heating

2: 88 percent / sodium methoxide / methanol / 1 h / -30 °C

3: 45 percent / pyridine / 25 h

With pyridine; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol;

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

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

p-toluenesulfonyl chloride

t-butyl (3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate

t-butyl (Z)-2-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenyl-2-acrylate

Downstream raw materials:

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

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

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

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