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

Base Information

• Chemical Name: 6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester
• CAS No.: 211801-64-8
• Molecular Formula: C₄₄H₅₇ClO₁₂Si
• Molecular Weight: 841.468

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 8 articles about 6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester 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:

p-methylphenyl-1-thio-β-D-galactopyranoside (1152-39-2,28244-98-6,121523-95-3,131488-68-1) → 6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (211801-64-8)

Guidance literature:

Multi-step reaction with 5 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

5: 1.) N-iodosuccinimide, TMSOTf, 4A molecular sieves, 2.) HgBr₂ / 1.) MeCN, from -20 deg C to RT, 2.) toluene, MeNO₂, 60 deg C

With 1H-imidazole; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl-carbodiimide; mercury dibromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9813616

Reference yield:

levulinic acid (123-76-2) → 6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (211801-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / DCC, 4-DMAP / CH₂Cl₂

2: 1.) N-iodosuccinimide, TMSOTf, 4A molecular sieves, 2.) HgBr₂ / 1.) MeCN, from -20 deg C to RT, 2.) toluene, MeNO₂, 60 deg C

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; dicyclohexyl-carbodiimide; mercury dibromide; In dichloromethane;

DOI:10.1021/ja9813616

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (211801-64-8)

Guidance literature:

Multi-step reaction with 4 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

4: 1.) N-iodosuccinimide, TMSOTf, 4A molecular sieves, 2.) HgBr₂ / 1.) MeCN, from -20 deg C to RT, 2.) toluene, MeNO₂, 60 deg C

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl-carbodiimide; mercury dibromide; In dichloromethane;

DOI:10.1021/ja9813616

upstream raw materials:

methyl 6-hydroxycaproate

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

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

levulinic acid

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

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