(4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

Base Information

• Chemical Name: (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester
• CAS No.: 869732-20-7
• Molecular Formula: C₃₈H₅₄N₂O₉
• Molecular Weight: 682.855
• Mol file: 869732-20-7.mol

Synonyms:(4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

Chemical Property of (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

There total 52 articles about (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl 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: 80.0%

(4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-3-one (869732-34-3) + Trichloroacetyl isocyanate (3019-71-4) → (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester (869732-20-7)

Guidance literature:

(4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,10,18,20-pentaen-3-one; Trichloroacetyl isocyanate; In dichloromethane; for 0.25h;

With potassium carbonate; In methanol; for 0.5h;

DOI:10.1021/ja055384d

Reference yield: 76.0%

(4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-hydroxy-13-(methoxymethoxy)-4,10,12,16-tetramethyl-14,19-trimethoxy-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-3-one (869732-34-3) + Trichloroacetyl isocyanate (3019-71-4) → (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid-20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester (869732-20-7)

Guidance literature:

(4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-hydroxy-13-(methoxymethoxy)-4,10,12,16-tetramethyl-14,19-trimethoxy-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-3-one; Trichloroacetyl isocyanate; In dichloromethane; for 0.25h; Inert atmosphere;

With potassium carbonate; In methanol; dichloromethane; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2014.03.020

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester (869732-20-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 99 percent / 1H-imidazole / dimethylformamide / 0 - 20 °C

2.1: DIBAL-H / toluene / 2 h / -78 °C

3.1: 19.8 g / benzene / 2 h / Heating

4.1: 95 percent / 4 Angstroem molecular sieves; Proton-Sponge / CH₂Cl₂ / 3 h / 20 °C

5.1: 99 percent / HCl / methanol / 1 h / 20 °C

6.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 4 h / 20 °C

7.1: Cp₂ZrHCl / toluene / 6 h / 50 °C

7.2: ZnMe₂ / toluene / -65 - 0 °C

7.3: 55 percent / toluene / 1 h / 0 °C

8.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9.1: aq. LiOH / tetrahydrofuran; methanol / 48 h

10.1: ethyl chloroformate; Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

10.2: 10.0 mg / NH₃ (gas) / CH₂Cl₂ / -20 °C

11.1: 83 percent / K₂CO₃; CuI; N,N'-dimethyl-1,2-ethanediamine / toluene / 36 h / 100 °C

12.1: 89 percent / HF*Pyr; pyridine / tetrahydrofuran / 36 h / 20 °C

13.1: CH₂Cl₂ / 0.25 h

13.2: 80 percent / K₂CO₃ / methanol / 0.5 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; copper(l) iodide; Schwartz's reagent; oxalyl dichloride; 4 A molecular sieve; Proton-Sponge; chloroformic acid ethyl ester; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N,N`-dimethylethylenediamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6.1: Swern oxidation;

DOI:10.1021/ja055384d

upstream raw materials:

(4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,10,18,20-pentaen-3-one

Trichloroacetyl isocyanate

(6S,2E)-ethyl 6-methoxy-2-methyl-7-oxohept-2-enoate

(6S,2E)-ethyl 6-methoxy-2-methyl-7-hydroxyhept-2-enoate