methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate

Base Information

• Chemical Name: methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate
• CAS No.: 351194-24-6
• Molecular Formula: C₄₄H₅₈O₆Si
• Molecular Weight: 711.026
• Mol file: 351194-24-6.mol

Synonyms:methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate

Chemical Property of methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate

There total 1 articles about methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate 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:

(Z)-3-(dimethyl(phenyl)silyl)oct-2-enal (351194-19-9) + 8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-3-en-2-one (351194-45-1) + bis(methyl-6-heptanoate)zinc → 7-{(1R,2R)-2-[(Z)-(R)-3-(Dimethyl-phenyl-silanyl)-1-hydroxy-oct-2-enyl]-3-oxo-8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-1-yl}-heptanoic acid methyl ester + methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate (351194-24-6) + 7-{(1S,2R)-2-[(Z)-(S)-3-(Dimethyl-phenyl-silanyl)-1-hydroxy-oct-2-enyl]-3-oxo-8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-1-yl}-heptanoic acid methyl ester + 7-{(1S,2S)-2-[(Z)-(S)-3-(Dimethyl-phenyl-silanyl)-1-hydroxy-oct-2-enyl]-3-oxo-8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-1-yl}-heptanoic acid methyl ester

Guidance literature:

With (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-[(1R)-1-phenethyl]amine; copper(II) bis(trifluoromethanesulfonate); In toluene; at -45 ℃; for 18h;

DOI:10.1021/ja015900+

Reference yield: 63.0%

methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate (351194-24-6) → methyl 7-[(1R,2R,3R)-2-[(Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl]-3-hydroxy-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate (351194-27-9)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at -30 ℃; for 3h;

DOI:10.1021/ja015900+

Reference yield:

methyl 7-[(1R,2S)-2-{(1R,2Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl}-3-oxo-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate (351194-24-6) → methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxy-1-octenyl]-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]-heptanoate (351194-38-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / Zn(BH₄)2 / diethyl ether / 3 h / -30 °C

2: Bu₄NF / tetrahydrofuran; dimethylsulfoxide; various solvent(s) / 0.33 h / 80 °C

3: DMAP; pyridine / 0.33 h

4: 63 percent / Pd(CH₃CN)2Cl₂ / tetrahydrofuran / 3 h

5: 90 percent / K₂CO₃ / methanol / 18 h

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide;

DOI:10.1021/ja015900+

upstream raw materials:

(Z)-3-(dimethyl(phenyl)silyl)oct-2-enal

8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-3-en-2-one

Downstream raw materials:

methyl 7-[(1R,2R,3R)-2-[(Z)-3-[dimethyl(phenyl)silyl]-1-hydroxy-2-octenyl]-3-hydroxy-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]heptanoate

prostaglandin E₁ methyl ester

methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxy-1-octenyl]-8,8-diphenyl-6,10-dioxaspiro[4.5]dec-1-yl]-heptanoate

7-[(1R,2R,3R)-3-Hydroxy-2-((E)-(S)-1-hydroxy-oct-2-enyl)-8,8-diphenyl-6,10-dioxa-spiro[4.5]dec-1-yl]-heptanoic acid methyl ester