Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester
• CAS No.: 128539-57-1
• Molecular Formula: C₃₆H₄₈O₉S
• Molecular Weight: 656.838
• Mol file: 128539-57-1.mol

Synonyms:

Chemical Property of Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester

There total 1 articles about Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester 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:

(1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one (122547-72-2) + phenylcarbonochloridothioate (1005-56-7) → Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester (128539-57-1)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1002/jlac.199719970135

Reference yield:

Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester (128539-57-1) → (E)-(1R,2S,5S,10S,11R,14S,15R,16S,18R)-1-Hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one (186768-50-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In toluene; at 110 ℃; for 0.25h; Yield given;

DOI:10.1002/jlac.199719970135

Reference yield:

Thiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18R)-1-hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-17-yl) ester O-phenyl ester (128539-57-1) → (E)-(2S,5S,10S,11R,14S,15R,16S)-10,11-Dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1(18),12-dien-3-one

Guidance literature:

Multi-step reaction with 4 steps

1: (Me₃Si)3SiH, AIBN / toluene / 0.25 h / 110 °C

2: 35 percent / PBr₃ / toluene / 0.67 h / -70 °C

3: 63 percent / p-TSA / methanol / Ambient temperature

4: 48 percent / NaBH₄ / dioxane / 0.75 h / 90 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; phosphorus tribromide; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; toluene;

DOI:10.1002/jlac.199719970135

upstream raw materials:

(1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

phenylcarbonochloridothioate

Downstream raw materials:

(E)-(1R,2S,5S,10S,11R,14S,15R,16S,18R)-1-Hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

(E)-(1R,2S,5S,10S,11R,14S,15R,16S)-10,11-Dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-ene-3,18-dione

(E)-(1R,2S,5S,10S,11R,14S,15R,16S,18R)-18-Hydroxy-10,11-dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one