β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 1443651-54-4
• Molecular Formula: C₃₃H₃₆O₉
• Molecular Weight: 576.643

Synonyms:β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Chemical Property of β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

There total 12 articles about β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside 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: 90.0%

β-L-2,3-dehydro-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-52-2) → β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-54-4)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; for 6h; Reflux;

DOI:10.1002/chem.201204545

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-54-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

2.1: acetic acid / 120 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

5.1: diethylzinc / tetrahydrofuran / 4 h / Molecular sieve; Inert atmosphere

5.2: Inert atmosphere; Molecular sieve

6.1: potassium carbonate / methanol / Inert atmosphere

7.1: pyridine / dichloromethane / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

9.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

10.1: methanol; triethylamine / Inert atmosphere

11.1: toluene-4-sulfonic acid hydrazide; sodium acetate / water; 1,2-dimethoxyethane / 6 h / Reflux

With pyridine; methanol; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 9.1: |Mitsunobu Displacement;

DOI:10.1002/chem.201204545

Reference yield:

benzyl 2,3-O-isopropylidene-4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside (316157-01-4) → β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-54-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: acetic acid / 120 h / 20 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

4.1: diethylzinc / tetrahydrofuran / 4 h / Molecular sieve; Inert atmosphere

4.2: Inert atmosphere; Molecular sieve

5.1: potassium carbonate / methanol / Inert atmosphere

6.1: pyridine / dichloromethane / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

8.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: methanol; triethylamine / Inert atmosphere

10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / water; 1,2-dimethoxyethane / 6 h / Reflux

With pyridine; methanol; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; potassium carbonate; acetic acid; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; 8.1: |Mitsunobu Displacement;

DOI:10.1002/chem.201204545

upstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl 2,3-O-isopropylidene-4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside

benzyl 4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside

C₂₂H₂₄O₇

Downstream raw materials:

4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

C₅₃H₆₅IO₁₃SSi

4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-α-L-rhamnopyranoside

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