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

Base Information

Chemical Name: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
CAS No.:270087-62-2
Molecular Formula:C₅₅H₆₁ClO₁₃S
Molecular Weight:997.601
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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: 77.0%

: 254444-15-0
Phenyl 3,4,6-tri-O-benzyl-1-seleno-2-O-allyloxycarbonyl-α-D-mannopyranoside

: 270087-62-2
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

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1016/S0957-4166(99)00519-4

Reference yield:

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

: 270087-62-2
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

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 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;
DOI:10.1016/S0957-4166(99)00519-4

Reference yield:

: 29073-91-4,55865-04-8,138196-19-7
1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

: 270087-62-2
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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 1H-imidazole; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 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;
DOI:10.1016/S0957-4166(99)00519-4