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

Base Information

Chemical Name: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
CAS No.:209113-73-5
Molecular Formula:C₆₇H₆₆O₂₃
Molecular Weight:1239.25
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 88.0%

: 701-99-5
Phenoxyacetyl chloride

: 209113-72-4
3,4,5-trimethoxyphenyl 6-O-(5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

: 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

Guidance literature:: With pyridine; In dichloromethane;
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

: 209113-73-5
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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 209113-60-0
ethyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-α/β-D-erythrofuranoside

: 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

Guidance literature:: Multi-step reaction with 6 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

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