methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Base Information

Chemical Name:methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate
CAS No.:61218-10-8
Molecular Formula:C₂₁H₃₄O₇
Molecular Weight:398.497
Hs Code.:

Synonyms:methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

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Chemical Property of methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

There total 30 articles about methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate 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:

: 102276-55-1
(Z)-7-[(1R,2S,3R,5S)-5-Acetoxy-2-(1-methoxy-1-methyl-ethoxymethyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

: 61218-10-8
methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at -5 ℃; Yield given;
DOI:10.1021/jm00179a011

Reference yield:

: 136235-73-9
(2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol

: 61218-10-8
methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Guidance literature:: Multi-step reaction with 20 steps

1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C

1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C

2.1: pyridinium p-toluenesulfonate / CHCl₃ / 12 h / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: Ph₃P / CH₂Cl₂ / 12 h / 20 °C

4.1: benzene / 7 h / 65 °C

5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 °C

7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C

8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9.1: Dess-Martin reagent / CH₂Cl₂ / 1 h / 0 °C

10.1: Ni(cod)2; PPh₃; i-Bu₂-ALAC / toluene / 2 h / 0 °C

11.1: imidazole / dimethylformamide / 7 h / 20 °C

12.1: O₃; O₂ / CH₂Cl₂ / -78 °C

12.2: PPh₃ / CH₂Cl₂ / 12 h / 20 °C

13.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

13.2: tetrahydrofuran / 0.25 h

14.1: methanol; diethyl ether / 0 °C

15.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

16.1: DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

17.1: Dowex₅₀^W / methanol / 0.5 h / 50 °C

18.1: Et₃N; DMAP / CH₂Cl₂ / 36 h / 20 °C

19.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

20.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C

With pyridine; 1H-imidazole; dmap; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; n-butyllithium; diisobutylaluminium acetylacetonate; 4 A molecular sieve; Dowex₅₀^W; potassium tert-butylate; tetrabutyl ammonium fluoride; oxygen; sodium acetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1248/cpb.48.1753

Reference yield:

: 193476-13-0
(2S,3R)-5-tert-butyldimethylsilyloxy-2-ethenylpentan-1,3-diol

: 61218-10-8
methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Guidance literature:: Multi-step reaction with 19 steps

1.1: pyridinium p-toluenesulfonate / CHCl₃ / 12 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: Ph₃P / CH₂Cl₂ / 12 h / 20 °C

3.1: benzene / 7 h / 65 °C

4.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

5.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 °C

6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

6.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C

7.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: Dess-Martin reagent / CH₂Cl₂ / 1 h / 0 °C

9.1: Ni(cod)2; PPh₃; i-Bu₂-ALAC / toluene / 2 h / 0 °C

10.1: imidazole / dimethylformamide / 7 h / 20 °C

11.1: O₃; O₂ / CH₂Cl₂ / -78 °C

11.2: PPh₃ / CH₂Cl₂ / 12 h / 20 °C

12.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

12.2: tetrahydrofuran / 0.25 h

13.1: methanol; diethyl ether / 0 °C

14.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

15.1: DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

16.1: Dowex₅₀^W / methanol / 0.5 h / 50 °C

17.1: Et₃N; DMAP / CH₂Cl₂ / 36 h / 20 °C

18.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

19.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C

With pyridine; 1H-imidazole; dmap; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; n-butyllithium; diisobutylaluminium acetylacetonate; 4 A molecular sieve; Dowex₅₀^W; potassium tert-butylate; tetrabutyl ammonium fluoride; oxygen; sodium acetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1248/cpb.48.1753