(4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione

Base Information

• Chemical Name: (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione
• CAS No.: 845780-43-0
• Molecular Formula: C₁₉H₂₆O₅S
• Molecular Weight: 366.478
• Mol file: 845780-43-0.mol

Synonyms:(4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione

Chemical Property of (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione

There total 4 articles about (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione 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: 79.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (2R,3R,4R)-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentane-1,3-diol (845780-30-5) → (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione (845780-43-0)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 - 60 ℃; for 2.5h;

DOI:10.1021/ol0478279

Reference yield:

(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde (845780-55-4) → (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione (845780-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

2: 89 percent / lithium borohydride / methanol; diethyl ether / 2.5 h / 0 - 20 °C

3: 79 percent / DMAP / tetrahydrofuran / 2.5 h / 20 - 60 °C

With dmap; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol0478279

Reference yield:

(2R)-2-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]propan-1-ol (845780-29-2) → (4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione (845780-43-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Dess-Martin periodinane / CH₂Cl₂

2: 83 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

3: 89 percent / lithium borohydride / methanol; diethyl ether / 2.5 h / 0 - 20 °C

4: 79 percent / DMAP / tetrahydrofuran / 2.5 h / 20 - 60 °C

With dmap; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol0478279

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

(2R,3R,4R)-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentane-1,3-diol

(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

(2R)-2-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]propan-1-ol

Downstream raw materials:

(2S,3R,4R,6S,9R,10S,11S,12S)-9,11,13-tris(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyltridecan-1-ol

1-methoxy-4-{(1R,2S)-2-methyl-1-[(1R,3S,6R,7S,8S,9S)-6,8,10-tris(tert-butyldimethylsilanyloxy)-1,3,7,9-tetramethyldecyl]but-3-enyloxymethyl}benzene

(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-[(1R,3S,6R,7S,8S,9S)-6,8,10-tris(tert-butyldimethylsilanyloxy)-1,3,7,9-tetramethyldecyl]-[1,3]dioxane

(2S,3S,4S,5R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-ol