p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside
• CAS No.: 211801-72-8
• Molecular Formula: C₄₄H₅₁ClO₉SSi
• Molecular Weight: 819.488
• Mol file: 211801-72-8.mol

Synonyms:p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

There total 6 articles about p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside 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: 83.0%

levulinic acid (123-76-2) + Chloro-acetic acid (2S,3R,4S,5S,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-3-yl ester → p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside (211801-72-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/ja9813616

Reference yield:

p-methylphenyl-1-thio-β-D-galactopyranoside (1152-39-2,28244-98-6,121523-95-3,131488-68-1) → p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside (211801-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / imidazole / dimethylformamide

2: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) toluene, benzene, reflux, 2.) DMF, 60 deg C

3: 52 percent / Et₃N / CH₂Cl₂ / -20 - 20 °C

4: 83 percent / DCC, 4-DMAP / CH₂Cl₂

With 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9813616

Reference yield:

p-methoxybenzyl chloride (824-94-2) → p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside (211801-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) toluene, benzene, reflux, 2.) DMF, 60 deg C

2: 52 percent / Et₃N / CH₂Cl₂ / -20 - 20 °C

3: 83 percent / DCC, 4-DMAP / CH₂Cl₂

With dmap; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/ja9813616

upstream raw materials:

levulinic acid

p-methylphenyl-1-thio-β-D-galactopyranoside

p-methoxybenzyl chloride

tert-butylchlorodiphenylsilane

Downstream raw materials:

6-[(2R,3R,4S,5S,6R)-4-((4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

6-[(2R,3R,4R,5S,6R)-4-((4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside