(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

Base Information

• Chemical Name: (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
• CAS No.: 186768-52-5
• Molecular Formula: C₂₈H₄₂O₆
• Molecular Weight: 474.638
• Mol file: 186768-52-5.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 64.0%

(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 (186768-51-4) → (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 (186768-52-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1002/jlac.199719970135

Reference yield: 13.0%

3,5-dideoxy-4-oxosoraphen tosylhydrazone → (E)-(1S,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-en-3-one + (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 (186768-52-5) + (E)-(1R,2S,5S,10S,11R,14S,15R,16S,18S)-18-Hydroxy-10,11-dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

Guidance literature:

With sodium cyanoborohydride; toluene-4-sulfonic acid; In 1,4-dioxane; N,N-dimethyl-formamide; at 110 ℃; for 4h;

DOI:10.1002/jlac.199719970135

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) → (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 (186768-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂

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

3: 35 percent / PBr₃ / toluene / 0.67 h / -70 °C

4: 64 percent / NaBH₄ / tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; phosphorus tribromide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/jlac.199719970135

upstream raw materials:

(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

(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

(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

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