(3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol
• CAS No.: 913258-10-3
• Molecular Formula: C₂₀H₃₂O₅SSi
• Molecular Weight: 412.623
• Mol file: 913258-10-3.mol

Synonyms:(3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property of (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol

There total 4 articles about (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol 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: 92.3%

(3aR,4R,5R,6aS)-4-(phenylsulfonyl)methyl-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one (913258-09-0) → (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol (913258-10-3)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -75 ℃; for 2h;

DOI:10.1002/ejoc.200600749

Reference yield:

(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one (913258-07-8) → (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol (913258-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 71.6 percent / PPh₃; DIAD / CH₂Cl₂; tetrahydrofuran / 40 h / 20 - 40 °C

2: 94.8 percent / magnesium monoperoxyphthalate hexahydrate / CH₂Cl₂; H₂O / 1.08 h

3: 92.3 percent / DIBALH / tetrahydrofuran; toluene / 2 h / -75 °C

With di-isopropyl azodicarboxylate; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1002/ejoc.200600749

Reference yield:

(3aR,4R,5R,6aS)-4-(phenylthio)methyl-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one (913258-08-9) → (3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol (913258-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94.8 percent / magnesium monoperoxyphthalate hexahydrate / CH₂Cl₂; H₂O / 1.08 h

2: 92.3 percent / DIBALH / tetrahydrofuran; toluene / 2 h / -75 °C

With diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1002/ejoc.200600749

upstream raw materials:

(3aR,4R,5R,6aS)-4-(phenylsulfonyl)methyl-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-4-(phenylthio)methyl-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-one

thiophenol

Downstream raw materials:

(1R,3S,4R,5R)-4-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-5-[(phenylsulfonyl)methyl]cyclopentan-1,3-diol

(1S,2R,3R,4R)-2-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-3-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol

(1R,2R,3R,4S)-3-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-2-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol

1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane