(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

Base Information

• Chemical Name: (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
• CAS No.: 869732-34-3
• Molecular Formula: C₃₇H₅₃NO₈
• Molecular Weight: 639.83

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of (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

There total 50 articles about (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 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%

(4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tertbutyldimethylsilyloxy)-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 (869732-19-4) → (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)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In acetonitrile; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2014.03.020

Reference yield: 89.0%

(4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-2-aza-bicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-3-one (869732-19-4) → (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)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 36h;

DOI:10.1021/ja055384d

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (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)

Guidance literature:

Multi-step reaction with 12 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

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,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-3-one

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

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

3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde

Downstream raw materials:

(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

(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

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