(1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate

Base Information

• Chemical Name: (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate
• CAS No.: 1392445-52-1
• Molecular Formula: C₂₆H₃₀INO₅
• Molecular Weight: 563.432

Synonyms:(1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate

Chemical Property of (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate

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Technology Process of (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate

There total 19 articles about (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11⁽¹⁵⁾-trien-12-yl-4-nitrobenzoate 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:

(3Z,7E,11S,12R,14S)-14-hydroxy-15-iodo-4,8,11,12-tetramethylbicyclo[9.3.1]pentadeca-1(15),3,7-trien-2-one (1392445-36-1) + 4-nitro-benzoic acid (62-23-7) → (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11(15)-trien-12-yl-4-nitrobenzoate (1392445-52-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol3017116

Reference yield:

(S,2Z,6E)-10-((R)-4-hydroxybutan-2-yl)-3,7,10-trimethylcyclododeca-2,6-dien-11-ynone (1392445-67-8) → (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11(15)-trien-12-yl-4-nitrobenzoate (1392445-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4-methylmorpholine N-oxide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 2 h / 20 °C / Inert atmosphere

2.1: magnesium iodide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; diethylazodicarboxylate / benzene / 0 °C / Inert atmosphere

With 4-methylmorpholine N-oxide; triphenylphosphine; magnesium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; benzene; 3.1: Mitsunobu reaction;

DOI:10.1021/ol3017116

Reference yield:

(R)-3-((S,5Z,9E)-1,6,10-trimethyl-4-oxocyclododeca-5,9-dien-2-ynyl)butanal (1392445-35-0) → (1S,4E,8Z,12R,14R)-15-iodo-1,4,8,14-tetramethyl-10-oxobicyclo[9.3.1]pentadeca-4,8,11(15)-trien-12-yl-4-nitrobenzoate (1392445-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium iodide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

2: triphenylphosphine; diethylazodicarboxylate / benzene / 0 °C / Inert atmosphere

With triphenylphosphine; magnesium iodide; diethylazodicarboxylate; In tetrahydrofuran; benzene; 2: Mitsunobu reaction;

DOI:10.1021/ol3017116

upstream raw materials:

(4Z)-6-[(4-methoxybenzyl)oxy]-4-methylhex-4-enal

methyl 2-((3R,4S)-4-methyl-4-vinyltetrahydrofuran-3-yl)acetate

2-((3R,4S)-4-methyl-4-vinyltetrahydrofuran-3-yl)ethanol

2-((3R,4S)-4-methyl-4-vinyltetrahydrofuran-3-yl)ethyl acetate

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