ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
• CAS No.: 270087-63-3
• Molecular Formula: C₅₁H₅₇ClO₁₁S
• Molecular Weight: 913.526

Synonyms:ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

There total 11 articles about ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside 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: 75.0%

ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(2-O-allyloxycarbonyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (270087-62-2) → ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (270087-63-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimedone; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1016/S0957-4166(99)00519-4

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (270087-63-3)

Guidance literature:

Multi-step reaction with 9 steps

1: K₂CO₃ / methanol / 7 h / 20 °C

2: imidazole / tetrahydrofuran / 2 h / 20 °C

3: tetrabutylammonium iodide; NaH / dimethylformamide / 14 h / 20 °C

4: 72 percent / HgBr₂; 4A/5A MS / acetonitrile / 4.5 h / 60 °C

5: K₂CO₃ / methanol / 14 h / 20 °C

6: 0.88 g / pyridine / CH₂Cl₂ / 1.25 h / 0 °C

7: 87 percent / 48 percent aq. HF / acetonitrile / 1 h / 20 °C

8: 77 percent / 4A MS; N-iodosuccinimide; TMSOTf / CH₂Cl₂; diethyl ether / 0.25 h / 20 °C

9: 75 percent / dimedone; Pd(PPh₃)4 / tetrahydrofuran / 14 h / 20 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dimedone; mercury dibromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Deacetylation / 2: Etherification / 3: Benzylation / 4: Thioetherification / 5: Deacetylation / 6: Acetylation / 7: Desilylation / 8: Condensation / 9: Deesterification;

DOI:10.1016/S0957-4166(99)00519-4

Reference yield:

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside (270087-63-3)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / tetrahydrofuran / 2 h / 20 °C

2: tetrabutylammonium iodide; NaH / dimethylformamide / 14 h / 20 °C

3: 72 percent / HgBr₂; 4A/5A MS / acetonitrile / 4.5 h / 60 °C

4: K₂CO₃ / methanol / 14 h / 20 °C

5: 0.88 g / pyridine / CH₂Cl₂ / 1.25 h / 0 °C

6: 87 percent / 48 percent aq. HF / acetonitrile / 1 h / 20 °C

7: 77 percent / 4A MS; N-iodosuccinimide; TMSOTf / CH₂Cl₂; diethyl ether / 0.25 h / 20 °C

8: 75 percent / dimedone; Pd(PPh₃)4 / tetrahydrofuran / 14 h / 20 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dimedone; mercury dibromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Etherification / 2: Benzylation / 3: Thioetherification / 4: Deacetylation / 5: Acetylation / 6: Desilylation / 7: Condensation / 8: Deesterification;

DOI:10.1016/S0957-4166(99)00519-4

upstream raw materials:

ethyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-O-(2-O-allyloxycarbonyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

(2'S,3'S) ethyl 2-O-chloroacetyl-3-O,4-O-[2',3'-dimethoxybutan-2',3'-diyl]-1-thio-α-D-mannopyranoside

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