benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

Base Information

Chemical Name:benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside
CAS No.:316188-22-4
Molecular Formula:C₅₉H₆₀O₁₄S
Molecular Weight:1025.18
Hs Code.:

Synonyms:benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

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Chemical Property of benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

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Technology Process of benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

There total 10 articles about benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside 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: 55.0%

: benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside

: 316188-21-3
ethyl 2,4,6-tri-O-benzyl-3-O-(carboxyacetyl)-1-thio-α-D-mannopyranoside

: 316188-22-4
benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U

Reference yield:

: 7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3
ethyl 1-thio-α-D-mannopyranoside

: 316188-22-4
benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

2: 87 percent / TsOH / 24 h / 20 °C

3: 84 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4: 94 percent / NaH / dimethylformamide / 1 h / 20 °C

5: 96 percent / AcOH / H₂O / 2.5 h / 70 °C

6: 80 percent / Bu₄NHSO₄; NaOH / H₂O; CH₂Cl₂ / 24 h / Heating

7: 62 percent / DCC; 1-hydroxy-1H-benzotriazole / CH₂Cl₂ / 49 h / 0 - 20 °C

8: 95 percent / CF₃COOH / CH₂Cl₂ / 3 h / 20 °C

9: 55 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: acetalization / 3: ether cleavage / 4: Alkylation / 5: acetal cleavage / 6: Alkylation / 7: Acylation / 8: ester cleavage / 9: Acylation;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U

Reference yield:

: 100-39-0
benzyl bromide

: 316188-22-4
benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[3-(ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-3-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / NaH / dimethylformamide / 1 h / 20 °C

2: 96 percent / AcOH / H₂O / 2.5 h / 70 °C

3: 80 percent / Bu₄NHSO₄; NaOH / H₂O; CH₂Cl₂ / 24 h / Heating

4: 62 percent / DCC; 1-hydroxy-1H-benzotriazole / CH₂Cl₂ / 49 h / 0 - 20 °C

5: 95 percent / CF₃COOH / CH₂Cl₂ / 3 h / 20 °C

6: 55 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; 1: Alkylation / 2: acetal cleavage / 3: Alkylation / 4: Acylation / 5: ester cleavage / 6: Acylation;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U