(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate

Base Information

• Chemical Name: (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate
• CAS No.: 637740-86-4
• Molecular Formula: C₄₇H₆₃IO₁₀Si
• Molecular Weight: 943.001

Synonyms:(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate

Chemical Property of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate

Chemical Property:

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Technology Process of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate

There total 5 articles about (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate 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: 66.0%

(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol (331626-81-4) + (E)-3-(4-Iodo-1,3-dimethyl-2-oxo-cyclohex-3-enyl)-2-methyl-acrylic acid (637741-40-3) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate (637740-86-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 5h; Heating;

DOI:10.1039/b305818b

Reference yield:

3-Iodo-2,6-dimethyl-cyclohex-2-enone (81465-44-3) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate (637740-86-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / aq. NaOH / dioxane / 0.5 h / 20 °C

2: 92 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3: 97 percent / toluene / 20 h / Heating

4: 54 percent / iodotrimethylsilane / 5 h / Heating

5: 66 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; N,N-dimethylaminopyridine / CH₂Cl₂ / 5 h / Heating

With dmap; sodium hydroxide; oxalyl dichloride; trimethylsilyl iodide; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; dichloromethane; toluene; 2: Swern oxidation;

DOI:10.1039/b305818b

Reference yield:

4-iodo-1,3-dimethyl-2-oxo-cyclohex-3-enecarbaldehyde (637741-38-9) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E)-2-methyl-3-(1,3-dimethyl-2-oxo-4-iodo-3-cyclohexenyl)propenoate (637740-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / toluene / 20 h / Heating

2: 54 percent / iodotrimethylsilane / 5 h / Heating

3: 66 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; N,N-dimethylaminopyridine / CH₂Cl₂ / 5 h / Heating

With dmap; trimethylsilyl iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene;

DOI:10.1039/b305818b

upstream raw materials:

(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol

(E)-3-(4-Iodo-1,3-dimethyl-2-oxo-cyclohex-3-enyl)-2-methyl-acrylic acid

3-Iodo-2,6-dimethyl-cyclohex-2-enone

4-iodo-1,3-dimethyl-2-oxo-cyclohex-3-enecarbaldehyde

Downstream raw materials:

3-{4-[4-(4-methoxy-benzyloxy)-1,3,5-trimethyl-pentadec-1-enyl]-1,3-dimethyl-2-oxo-cyclohex-3-enyl}-2-methyl-acrylic acid 3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E)-2-methyl-3-[1,3-dimethyl-2-oxo-4-[(1E,3S,4R,5S)-1,3,5-trimethyl-4-(4-methoxybenzyloxy)-1-pentadecenyl]-3-cyclohexenyl]propenoate

(E)-3-{4-[(E)-(3S,4R,5S)-4-(4-Methoxy-benzyloxy)-1,3,5-trimethyl-pentadec-1-enyl]-1,3-dimethyl-2-oxo-cyclohex-3-enyl}-2-methyl-acrylic acid (1R,2R,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butyl ester

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