2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

Base Information

• Chemical Name: 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide
• CAS No.: 866783-41-7
• Molecular Formula: C₂₉H₃₉NO₈
• Molecular Weight: 529.631

Synonyms:2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

Chemical Property of 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

There total 14 articles about 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide 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:

(3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-ol → 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide (866783-41-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / pyridine / 5 h / 20 °C

2: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

3: NaOMe / methanol / 18 h / 20 °C

4: PPTS / benzene / Heating

5: H₂; AcOH / Pd/C / ethanol / 10 h / 20 °C

6: imidazole / dimethylformamide / 3 h / 20 °C

7: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

8: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

9: 100 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

10: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C

11: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

12: aq. NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; various solvent(s) / 1 h / 20 °C / pH 7

13: TEA; EDCI; HOBt / CH₂Cl₂

14: 90 percent / aq. PPTS / acetone / 1 h / Heating

With pyridine; 1H-imidazole; sodium chlorite; 2-methyl-but-2-ene; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; TEA; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1055/s-2005-871960

Reference yield:

Acetic acid (3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl ester → 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide (866783-41-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

2: NaOMe / methanol / 18 h / 20 °C

3: PPTS / benzene / Heating

4: H₂; AcOH / Pd/C / ethanol / 10 h / 20 °C

5: imidazole / dimethylformamide / 3 h / 20 °C

6: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

7: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

8: 100 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

9: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C

10: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

11: aq. NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; various solvent(s) / 1 h / 20 °C / pH 7

12: TEA; EDCI; HOBt / CH₂Cl₂

13: 90 percent / aq. PPTS / acetone / 1 h / Heating

With 1H-imidazole; sodium chlorite; 2-methyl-but-2-ene; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; TEA; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1055/s-2005-871960

Reference yield:

1-((2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-propan-2-one → 2-[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide (866783-41-7)

Guidance literature:

Multi-step reaction with 11 steps

1: PPTS / benzene / Heating

2: H₂; AcOH / Pd/C / ethanol / 10 h / 20 °C

3: imidazole / dimethylformamide / 3 h / 20 °C

4: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

5: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

6: 100 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

7: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C

8: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

9: aq. NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; various solvent(s) / 1 h / 20 °C / pH 7

10: TEA; EDCI; HOBt / CH₂Cl₂

11: 90 percent / aq. PPTS / acetone / 1 h / Heating

With 1H-imidazole; sodium chlorite; 2-methyl-but-2-ene; 18-crown-6 ether; TEA; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1055/s-2005-871960

upstream raw materials:

(2R,3S,4R,5R,6S)-5-Methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-3,4-diol

(2R,3S,4R,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran

(2S,3S,4R,5S,6S)-2-Iodomethyl-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran

[(2R,3R,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-acetonitrile

Downstream raw materials:

2-[(2R,3R,4R,5R,6R)-6-((S)-1-Hydroxy-2-oxo-propyl)-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

2-{(2R,3R,4R,5R,6R)-3,4-Bis-(4-methoxy-benzyloxy)-6-[(S)-1-(4-methoxy-benzyloxy)-2-oxo-propyl]-5-methyl-tetrahydro-pyran-2-yl}-N-methoxy-N-methyl-acetamide

2-[(2R,3R,4R,5R,6R)-6-[(S)-[(2R,4S,5R,6R)-6-(4-Chloro-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

2-[6-[[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

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