(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate

Base Information

• Chemical Name: (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate
• CAS No.: 223564-97-4
• Molecular Formula: C₄₀H₅₈O₆Si
• Molecular Weight: 662.982
• Mol file: 223564-97-4.mol

Synonyms:(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate

Chemical Property of (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate

There total 6 articles about (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate 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: 36.0%

(2R,4R,2'R/S,6'S,8'S,9'S,11'R,1''S)-4-{8-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-9,11-dimethyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-2-ethyl-2-hydroxypent-1-yl acetate (337359-85-0) → (2'R,4'R,5'S,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate + (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate (223564-97-4)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; at 20 ℃; for 7h; Irradiation;

DOI:10.1039/b008159k

Reference yield:

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one (130514-54-4) → (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate (223564-97-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

2.1: Amberlite resin IR 118

3.1: 90 mg / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: H₂; K₂CO₃ / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C

5.1: 40 mg / pyridinium toluene-p-sulfonate / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 36 percent / PhI(OAc)2; I₂ / cyclohexane / 7 h / 20 °C / Irradiation

With dmap; n-butyllithium; [bis(acetoxy)iodo]benzene; Amberlite resin IR 118; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; ethyl acetate; pentane;

DOI:10.1039/b008159k

Reference yield:

(2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol (223564-85-0) → (2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methyl acetate (223564-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 mg / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

2: H₂; K₂CO₃ / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C

3: 40 mg / pyridinium toluene-p-sulfonate / CH₂Cl₂ / 0.5 h / 20 °C

4: 36 percent / PhI(OAc)2; I₂ / cyclohexane / 7 h / 20 °C / Irradiation

With dmap; [bis(acetoxy)iodo]benzene; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; Lindlar's catalyst; In dichloromethane; cyclohexane; ethyl acetate; pentane;

DOI:10.1039/b008159k

upstream raw materials:

(2R,4R,2'R/S,6'S,8'S,9'S,11'R,1''S)-4-{8-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-9,11-dimethyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-2-ethyl-2-hydroxypent-1-yl acetate

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one

(2R,4R)-8-{(3R,5S,6S)-6-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-ethyl-4-methyl-oct-7-yne-1,2,5-triol

(2R,4R,5S/R,2'S/R,3'R,5'S,6'S,1''S)-8-{6-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl}-2-ethyl-2,5-dihydroxy-4-methyloct-7-yn-1-yl acetate

Downstream raw materials:

(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methanol

(2'R,4'R,5'R,7'S,9'S,10'S,12'R,1''S)-{9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-en-2-yl}methanal

(2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene