methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside
CAS No.:204918-64-9
Molecular Formula:C₅₀H₅₀O₂₀
Molecular Weight:970.935
Hs Code.:

Synonyms:methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

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Chemical Property of methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

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Technology Process of methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

There total 17 articles about methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside 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: 80.0%

: 204918-48-9
1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside

: 204918-63-8
methyl (2,3-di-O-benzoyl-α-D-arabinofuranosyl)-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside

: 204918-64-9
methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -10 ℃;
DOI:10.1016/S0960-894X(98)00049-3

Reference yield:

: 61826-42-4
tetra-O-acetyl-D-arabinofuranose

: 204918-64-9
methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

2: 100 percent / CH₃ONa; methanol / 3 h / 20 °C

3: 83 percent / DMAP; pyridine / 3 h / 0 °C

4: 91 percent / pyridine / 3 h / 0 - 20 °C

5: 82 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

6: 95 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 - 20 °C

7: 80 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; methanol; dmap; N-iodo-succinimide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: deacetylation / 3: Substitution / 4: Substitution / 5: glycosylation / 6: desilylation / 7: glycosylation;
DOI:10.1021/ja993543l

Reference yield:

: 204918-51-4
methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside

: 204918-64-9
methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

2: 95 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 - 20 °C

3: 80 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

With N-iodo-succinimide; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: glycosylation / 2: desilylation / 3: glycosylation;
DOI:10.1021/ja993543l