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

Base Information

• Chemical Name: 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
• CAS No.: 866783-24-6
• Molecular Formula: C₂₉H₃₉NO₉
• Molecular Weight: 545.63
• Mol file: 866783-24-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 17 articles about 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 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: 78.0%

2-[6-[2-(tert-butyl-dimethyl-silanyloxy)-propenyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide → 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 (866783-24-6)

Guidance literature:

2-[6-[2-(tert-butyl-dimethyl-silanyloxy)-propenyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide; With pyridine; dihydrogen peroxide; methyltrioxorhenium(VII); In dichloromethane; at 0 - 20 ℃; for 4h;

With tetrabutyl ammonium fluoride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1055/s-2005-871960

Reference yield:

(3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-ol → 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 (866783-24-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / pyridine / 5 h / 20 °C

2.1: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

3.1: NaOMe / methanol / 18 h / 20 °C

4.1: PPTS / benzene / Heating

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

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

7.1: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

8.1: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

9.1: 100 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

10.1: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C

11.1: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

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

13.1: TEA; EDCI; HOBt / CH₂Cl₂

14.1: 90 percent / aq. PPTS / acetone / 1 h / Heating

15.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.33 h / -78 °C

15.2: 100 percent / 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / -78 °C

16.1: aq. H₂O₂; pyridine; methyltrioxorhenium / CH₂Cl₂ / 4 h / 0 - 20 °C

16.2: 78 percent / TBAF / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 1H-imidazole; sodium chlorite; 2-methyl-but-2-ene; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; sodium methylate; pyridinium p-toluenesulfonate; methyltrioxorhenium(VII); 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,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 (866783-24-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

2.1: NaOMe / methanol / 18 h / 20 °C

3.1: PPTS / benzene / Heating

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

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

6.1: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

7.1: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

8.1: 100 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

9.1: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C

10.1: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

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

12.1: TEA; EDCI; HOBt / CH₂Cl₂

13.1: 90 percent / aq. PPTS / acetone / 1 h / Heating

14.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.33 h / -78 °C

14.2: 100 percent / 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / -78 °C

15.1: aq. H₂O₂; pyridine; methyltrioxorhenium / CH₂Cl₂ / 4 h / 0 - 20 °C

15.2: 78 percent / TBAF / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 1H-imidazole; sodium chlorite; 2-methyl-but-2-ene; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; sodium methylate; pyridinium p-toluenesulfonate; methyltrioxorhenium(VII); 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

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

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

(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

Downstream raw materials:

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

2-[(2R,3R,4R,5R,6R)-6-[(1S,4S,5R,6R)-10-Chloro-4-hydroxy-1-(4-methoxy-benzyloxy)-5-methyl-2-oxo-6-triethylsilanyloxy-decyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-N-methoxy-N-methyl-acetamide

C₆₃H₉₆ClIO₁₁Si₂