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

Base Information

• Chemical Name: (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester
• CAS No.: 197523-93-6
• Molecular Formula: C₂₁H₃₄O₇
• Molecular Weight: 398.497
• Mol file: 197523-93-6.mol

Synonyms:

Chemical Property of (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

There total 9 articles about (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 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: 98.0%

(Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (197523-92-5) → (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (197523-93-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 10 ℃; for 2h;

DOI:10.1135/cccc19971325

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (197523-93-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature

2: 91 percent / DIBAL / toluene / 0.75 h / -70 °C

3: 1.) t-BuOK / 1.) THF, 5 deg C, 15 min, 2.) THF, 5 deg C, 60 min

4: K₂CO₃ / acetone / 15 h / Ambient temperature

5: 90 percent / 4-dimethylpyridine, pyridine / 1.) diminished temp., 10 min, 2.) r.t., 60 min

6: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 10 °C

With pyridine; 4-dimethylpyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; 1,2-dichloro-ethane; acetone; toluene;

DOI:10.1135/cccc19971325

Reference yield:

<3aS(3aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one (39265-57-1) → (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (197523-93-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 65 percent / CH₃ONa / methanol / 1.33 h / Ambient temperature

3: 82 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature

4: 91 percent / DIBAL / toluene / 0.75 h / -70 °C

5: 1.) t-BuOK / 1.) THF, 5 deg C, 15 min, 2.) THF, 5 deg C, 60 min

6: K₂CO₃ / acetone / 15 h / Ambient temperature

7: 90 percent / 4-dimethylpyridine, pyridine / 1.) diminished temp., 10 min, 2.) r.t., 60 min

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 10 °C

With pyridine; 1H-imidazole; 4-dimethylpyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1135/cccc19971325

upstream raw materials:

(Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

3,4-dihydro-2H-pyran

<3aS(3aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one

(3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one