(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one
• CAS No.: 131543-66-3
• Molecular Formula: C₃₀H₃₀O₆S
• Molecular Weight: 518.631

Synonyms:(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

Chemical Property of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

There total 7 articles about (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one 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:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one (131543-66-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / CBr₄, Ph₃P / acetonitrile / 1 h / Ambient temperature

2: 80 percent / NaI / acetone / 1 h / Heating

4: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: 92 percent / titanium tetraisopropoxide, L-(+)-diethyl tartrate / CH₂Cl₂ / 11 h / -20 °C

6: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2.5 h

7: 1) sodium methoxide / 1) ethanol, 45 deg C, 0.5 h, 2) THF, 6 h

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium methylate; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00003a083

Reference yield:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(bromomethyl)-2H-cyclopentafuran-2-one (131543-59-4) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one (131543-66-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / NaI / acetone / 1 h / Heating

3: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: 92 percent / titanium tetraisopropoxide, L-(+)-diethyl tartrate / CH₂Cl₂ / 11 h / -20 °C

5: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2.5 h

6: 1) sodium methoxide / 1) ethanol, 45 deg C, 0.5 h, 2) THF, 6 h

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium methylate; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/jo00003a083

Reference yield:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one (131543-60-7) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one (131543-66-3)

Guidance literature:

Multi-step reaction with 5 steps

2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

3: 92 percent / titanium tetraisopropoxide, L-(+)-diethyl tartrate / CH₂Cl₂ / 11 h / -20 °C

4: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 2.5 h

5: 1) sodium methoxide / 1) ethanol, 45 deg C, 0.5 h, 2) THF, 6 h

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00003a083

upstream raw materials:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R,3R)-2,3-epoxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

thiophenol

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(bromomethyl)-2H-cyclopentafuran-2-one

Downstream raw materials:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylsulfinyl)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 131543-66-3 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

Send

Send

Metric Ton KG G Pound L ML

Send

Send