ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside
CAS No.:316188-20-2
Molecular Formula:C₃₆H₄₄O₈S
Molecular Weight:636.807
Hs Code.:

Synonyms:ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

There total 8 articles about ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-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: 62.0%

: 40052-13-9
mono-tert-butyl malonate

: 289057-12-1
ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 316188-20-2
ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 49h;
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

: 316188-20-2
ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 100-39-0
benzyl bromide

: 316188-20-2
ethyl 2,4,6-tri-O-benzyl-3-O-[3-(tert-butoxy)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 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

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