4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside

Base Information

• Chemical Name: 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside
• CAS No.: 1443651-46-4
• Molecular Formula: C₂₆H₃₈O₈Si
• Molecular Weight: 506.668

Synonyms:4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside

Chemical Property of 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside

There total 5 articles about 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-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: 86.0%

benzyl 2,3-O-carboxy-α-L-rhamnopyranoside (1443651-34-0) + 3-O-Acetyl-1,5-anhydro-4-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol (101856-97-7) → 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside (1443651-46-4)

Guidance literature:

benzyl 2,3-O-carboxy-α-L-rhamnopyranoside; With diethylzinc; In tetrahydrofuran; for 4h; Molecular sieve; Inert atmosphere;

3-O-Acetyl-1,5-anhydro-4-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol; With palladium diacetate; johnphos; In tetrahydrofuran; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201204545

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside (1443651-46-4)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; diethylzinc; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201204545

Reference yield:

benzyl 4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside (316157-02-5) → 4-O-(tert-butyldimethylsilyl)-β-L-2,3-dehydro-amicetopyranosyl-(1→4)-1-O-benzyl-2,3-O-carboxy-α-L-rhamnopyranoside (1443651-46-4)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; diethylzinc; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;

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

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

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

C₅₃H₆₅IO₁₃SSi

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