(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

Base Information

• Chemical Name: (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
• CAS No.: 869732-19-4
• Molecular Formula: C₄₃H₆₇NO₈Si
• Molecular Weight: 754.092

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 49 articles about (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 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: 83.0%

(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide (869732-09-2) → (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)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 100 ℃; for 36h;

DOI:10.1021/ja055384d

Reference yield: 82.0%

(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide (869732-09-2) → (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)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 100 ℃; for 36h; Inert atmosphere; Sealed tube;

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)-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)

Guidance literature:

Multi-step reaction with 11 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

With 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; 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:

(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide

(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,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

(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

C₄₁H₆₃NO₇Si

(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

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