(1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Base Information

• Chemical Name: (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione
• CAS No.: 1380327-88-7
• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.621

Synonyms:(1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Chemical Property of (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione

There total 42 articles about (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione 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: 83.0%

(1R,3R,4R,5S,9R,13R)-9-((benzyloxy)methyl)-3-(4-(3-(benzyloxy)phenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione → (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione (1380327-88-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; chemoselective reaction;

DOI:10.1016/j.tet.2014.11.026

Reference yield: 59.0%

C48H68O9Si (1380328-11-9) → (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione (1380327-88-7)

Guidance literature:

C₄₈H₆₈O₉Si; With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran;

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene;

With palladium 10% on activated carbon; hydrogen; In ethanol;

Reference yield:

(R)-2-((2R,3R)-7-(3-(benzyloxy)phenyl)-3-((4-methoxybenzyl)oxy)heptan-2-yl)oxirane (1380328-05-1) → (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione (1380327-88-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-butyllithium / tetrahydrofuran

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran

4.1: sulfur trioxide pyridine complex; triethylamine; dimethyl sulfoxide / dichloromethane

5.1: titanium tetrachloride; titanium(IV) isopropylate; silver(l) oxide; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane

6.1: trifluoroacetic acid; water / tetrahydrofuran / 23 h / 50 °C

7.1: Selectfluor / water; acetonitrile / 0.5 h / 4 °C

8.1: triethylamine; dmap; 2,4,6-trichlorobenzoyl chloride / toluene

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1 h / 20 °C / pH 7.2

10.1: sodium periodate; potassium permanganate / aq. phosphate buffer; tert-butyl alcohol / 0.75 h / 20 °C / pH 7.2 / Inert atmosphere

11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 20 °C

11.2: 2.25 h / 20 °C

12.1: palladium 10% on activated carbon; hydrogen / ethanol

With titanium(IV) isopropylate; dmap; potassium permanganate; sodium periodate; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; (S)-[1,1']-binaphthalenyl-2,2'-diol; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; Selectfluor; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; aq. phosphate buffer; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 4.1: |Parikh-Doering Oxidation / 8.1: |Yamaguchi Lactonization / 11.1: |Yamaguchi Lactonization / 11.2: |Yamaguchi Lactonization;

DOI:10.1016/j.tet.2014.11.026

upstream raw materials:

C₃₈H₅₆O₄S₂

C₃₂H₄₄O₄

C₅₁H₆₄O₈

C₄₈H₆₈O₉Si

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