3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

Base Information

Chemical Name:3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside
CAS No.:209113-74-6
Molecular Formula:C₆₀H₆₀O₂₃
Molecular Weight:1149.12
Hs Code.:

Synonyms:3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

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Chemical Property of 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

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Technology Process of 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

There total 14 articles about 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-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: 86.0%

: 209113-73-5
3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

: 209113-74-6
3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; isopropyl alcohol;
DOI:10.1016/S0040-4039(98)00673-X

Reference yield:

: 35784-51-1
ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

: 209113-74-6
3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / triflic acid; N-iodosuccinimide / 1,2-dichloro-ethane; diethyl ether / 0.03 h / 0 °C

2: N-iodosuccinimide; triflic acid / CH₂Cl₂; H₂O / 20 °C

3: Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

4: 63 percent / BF₃*OEt₂ / CH₂Cl₂; tetrahydrofuran / 0.5 h / 20 °C

5: 88 percent / MeONa / methanol; CH₂Cl₂ / 2 h / 20 °C

6: 88 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

7: 86 percent / H₂ / Pd/C / propan-2-ol; ethyl acetate; pyridine / 48 h / 20 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; sodium methylate; caesium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; isopropyl alcohol; 1: Condensation / 2: desulfation / 3: Condensation / 4: Condensation / 5: Hydrolysis / 6: Acylation / 7: Hydrogenolysis;
DOI:10.1016/S0040-4020(99)00527-X

Reference yield:

: 209113-70-2
3,4,5-trimethoxyphenyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside

: 209113-74-6
3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / MeONa / methanol; CH₂Cl₂ / 2 h / 20 °C

2: 88 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

3: 86 percent / H₂ / Pd/C / propan-2-ol; ethyl acetate; pyridine / 48 h / 20 °C

With pyridine; hydrogen; sodium methylate; palladium on activated charcoal; In pyridine; methanol; dichloromethane; ethyl acetate; isopropyl alcohol; 1: Hydrolysis / 2: Acylation / 3: Hydrogenolysis;
DOI:10.1016/S0040-4020(99)00527-X