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

Base Information

• Chemical Name: 4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-L-rhamnopyranoside
• CAS No.: 1443651-67-9
• Molecular Formula: C₄₀H₅₆O₁₃Si
• Molecular Weight: 772.962

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 17 articles about 4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-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:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-L-rhamnopyranoside (1443651-67-9)

Guidance literature:

Multi-step reaction with 14 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

12.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / -78 °C / Molecular sieve; Inert atmosphere

12.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

13.1: sodium hydrogencarbonate; lithium iodide / tetrahydrofuran / Inert atmosphere; Reflux

14.1: Raney-Ni / ethanol / 0.5 h / Inert atmosphere; Reflux

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; 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) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-L-rhamnopyranoside (1443651-67-9)

Guidance literature:

Multi-step reaction with 13 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

11.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / -78 °C / Molecular sieve; Inert atmosphere

11.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

12.1: sodium hydrogencarbonate; lithium iodide / tetrahydrofuran / Inert atmosphere; Reflux

13.1: Raney-Ni / ethanol / 0.5 h / Inert atmosphere; Reflux

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

DOI:10.1002/chem.201204545

Reference yield:

benzyl 4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside (316157-02-5) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-L-rhamnopyranoside (1443651-67-9)

Guidance literature:

Multi-step reaction with 12 steps

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

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

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

3.2: Inert atmosphere; Molecular sieve

4.1: potassium carbonate / methanol / Inert atmosphere

5.1: pyridine / dichloromethane / Inert atmosphere

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

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

8.1: methanol; triethylamine / Inert atmosphere

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

10.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / -78 °C / Molecular sieve; Inert atmosphere

10.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

11.1: sodium hydrogencarbonate; lithium iodide / tetrahydrofuran / Inert atmosphere; Reflux

12.1: Raney-Ni / ethanol / 0.5 h / Inert atmosphere; Reflux

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; sodium hydrogencarbonate; potassium carbonate; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; 7.1: |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-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-trichloroacetimidate-β-L-rhamnopyranoside

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