Carbonothioic acid, O-[3-hydroxy-2-[(2S,3S,4R,6S)-tetrahydro-4-hydroxy-2-(4-methoxyphen yl)-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-3-yl]propyl] O-phenyl ester

Base Information

• Chemical Name: Carbonothioic acid, O-[3-hydroxy-2-[(2S,3S,4R,6S)-tetrahydro-4-hydroxy-2-(4-methoxyphen yl)-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-3-yl]propyl] O-phenyl ester
• CAS No.: 922167-80-4
• Molecular Formula: C31H36O7S
• Molecular Weight: 552.689
• Mol file: 922167-80-4.mol

Synonyms:

Chemical Property of Carbonothioic acid, O-[3-hydroxy-2-[(2S,3S,4R,6S)-tetrahydro-4-hydroxy-2-(4-methoxyphen yl)-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-3-yl]propyl] O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbonothioic acid, O-[3-hydroxy-2-[(2S,3S,4R,6S)-tetrahydro-4-hydroxy-2-(4-methoxyphen yl)-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-3-yl]propyl] O-phenyl ester

There total 11 articles about Carbonothioic acid, O-[3-hydroxy-2-[(2S,3S,4R,6S)-tetrahydro-4-hydroxy-2-(4-methoxyphen yl)-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-3-yl]propyl] O-phenyl ester 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: 80.0%

2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propane-1,3-diol (922167-79-1) + phenylcarbonochloridothioate (1005-56-7) → thiocarbonic acid O-(3-hydroxy-2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propyl) ester O-phenyl ester (922167-80-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol0627956

Reference yield:

3-(4-methoxyphenyl)propional (20401-88-1) → thiocarbonic acid O-(3-hydroxy-2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propyl) ester O-phenyl ester (922167-80-4)

Guidance literature:

Multi-step reaction with 5 steps

1: (R)-BINOL; silver(I) oxide; TiCl₄ / Ti(Oi-Pr)4 / CH₂Cl₂ / cooling

2: Hoveyda-Grubbs second generation catalyst / CH₂Cl₂ / 24 h / 20 °C

3: triethylsilyl triflate; acetic acid / 1 h / 20 °C

4: potassium carbonate / methanol / 3 h / 20 °C

5: pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; triethylsilyl trifluoromethyl sulfonate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; potassium carbonate; acetic acid; silver(l) oxide; titanium(IV) isopropylate; Hoveyda-Grubbs catalyst second generation; In methanol; dichloromethane;

DOI:10.1016/j.tet.2007.02.028

Reference yield:

3-(p-methoxyphenyl)-1-propanol (5406-18-8) → thiocarbonic acid O-(3-hydroxy-2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propyl) ester O-phenyl ester (922167-80-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / triethylamine; sulfur trioxide pyridine complex; dimethylsulfoxide / CH₂Cl₂ / 0 - 20 °C

2: (R)-BINOL; silver(I) oxide; TiCl₄ / Ti(Oi-Pr)4 / CH₂Cl₂ / cooling

3: Hoveyda-Grubbs second generation catalyst / CH₂Cl₂ / 24 h / 20 °C

4: triethylsilyl triflate; acetic acid / 1 h / 20 °C

5: potassium carbonate / methanol / 3 h / 20 °C

6: pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; triethylsilyl trifluoromethyl sulfonate; (R)-1,1'-Bi-2-naphthol; sulfur trioxide pyridine complex; titanium tetrachloride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; titanium(IV) isopropylate; Hoveyda-Grubbs catalyst second generation; In methanol; dichloromethane;

DOI:10.1016/j.tet.2007.02.028

upstream raw materials:

2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propane-1,3-diol

phenylcarbonochloridothioate

(-)-(3S)-1-(4-methoxyphenyl)hex-5-en-3-ol

acetic acid 2-acetoxymethyl-6-hydroxy-8-(4-methoxy-phenyl)-oct-3-enyl ester

Downstream raw materials:

thiocarbonic acid O-{1-(4-methoxy-phenyl)-3,6-bis-[2-(4-methoxy-phenyl)-ethyl]-hexahydro-2,5,7-trioxa-benzocyclohepten-9-ylmethyl} ester O-phenyl ester

5-(4-methoxy-phenyl)-2,7-bis-[2-(4-methoxy-phenyl)-ethyl]-hexahydro-pyrano[4,3-b]pyran-4-carbaldehyde

5-(4-methoxy-phenyl)-2,7-bis-[2-(4-methoxy-phenyl)-ethyl]-hexahydro-pyrano[4,3-b]pyran-4-carbaldehyde

1-(4-methoxy-phenyl)-3,6-bis-[2-(4-methoxy-phenyl)-ethyl]-9-methylene-hexahydro-2,5,7-trioxa-benzocycloheptene