p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside
• CAS No.: 870001-62-0
• Molecular Formula: C₄₂H₄₉N₃O₇SSi
• Molecular Weight: 768.018

Synonyms:p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

There total 6 articles about p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-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: 90.0%

(2S,3R,4R,5S,6R)-3-Azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-ol (870001-83-5) + levulinic acid (123-76-2) → p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (870001-62-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol052130o

Reference yield:

p-tolyl 3-O-acetyl-1,2-deoxy-4,6-O-(p-methoxybenzylidene)-2-phthalimido-1-thio-β-D-glucopyranoside → p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (870001-62-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / Bu₂BOTf; BH₃*THF / tetrahydrofuran; CH₂Cl₂ / 1.5 h / -20 - -5 °C

2: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

3: NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

4: ethylenediamine / butan-1-ol / 12 h / 100 °C

5: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

6: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; borane-THF; di-n-butylboryl trifluoromethanesulfonate; triflic azide; sodium methylate; potassium carbonate; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/ol052130o

Reference yield:

Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester (870001-81-3) → p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (870001-62-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

3: ethylenediamine / butan-1-ol / 12 h / 100 °C

4: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

5: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; triflic azide; sodium methylate; potassium carbonate; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/ol052130o

upstream raw materials:

(2S,3R,4R,5S,6R)-3-Azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-ol

levulinic acid

Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxy-benzyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Downstream raw materials:

methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-amino-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

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