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

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 870001-88-0
• Molecular Formula: C₄₃H₆₃N₃O₁₅Si₂
• Molecular Weight: 918.155

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

Chemical Property of (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 17 articles about (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 84.0%

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) (870001-64-2) → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (870001-88-0)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 7h;

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 → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (870001-88-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / Bu₂BOTf; BH₃*THF / tetrahydrofuran; CH₂Cl₂ / 1.5 h / -20 - -5 °C

2.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

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

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

5.1: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

6.1: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

7.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

7.2: 25 percent / CH₂Cl₂ / 20 h / -60 - 20 °C

8.1: 84 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 7 h / 0 °C

With 1H-imidazole; dmap; borane-THF; ammonium cerium(IV) nitrate; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; triflic azide; sodium methylate; potassium carbonate; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; 2,6-di-tert-butyl-4-methylpyridine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 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) → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (870001-88-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

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

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

4.1: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

5.1: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

6.2: 25 percent / CH₂Cl₂ / 20 h / -60 - 20 °C

7.1: 84 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 7 h / 0 °C

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; triflic azide; sodium methylate; potassium carbonate; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; 2,6-di-tert-butyl-4-methylpyridine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1021/ol052130o

upstream 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)

methyl 2-O-acetyl-α-D-3,6-glucuronolactone

methyl 2-O-acetyl-4-(p-methoxybenzyl)-α-D-3,6-glucuronolactone

(2S,3S,4S,5R,6S)-4,5-Diacetoxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

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