4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol

Base Information

• Chemical Name: 4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol
• CAS No.: 86021-78-5
• Molecular Formula: C₁₄H₁₈O₃S
• Molecular Weight: 266.361
• DSSTox Substance ID: DTXSID70560065

Synonyms:86021-78-5;4-((Phenylthio)methyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol;DTXSID70560065;4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol

Chemical Property of 4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 266.09766561
• Heavy Atom Count: 18
• Complexity: 280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(CC(C2CSC3=CC=CC=C3)O)OC1O

Technology Process of 4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol

There total 12 articles about 4-[(Phenylsulfanyl)methyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol 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: 75.0%

(3aS,5S,6aR)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4,91739-11-6,118919-52-1) → (3aS,5S,6aR)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol (86021-78-5,105455-57-0,105455-58-1,118919-53-2,118919-54-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(01)80897-2

Reference yield: 75.0%

4β-(thiophenoxymethyl)-5α-hydroxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran-2-one (86021-69-4,91739-11-6,118919-52-1) → 4β-(thiophenoxymethyl)-2ξ,5α-dihydroxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran-2-one (86021-78-5,105455-57-0,105455-58-1,118919-53-2,118919-54-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

(3aR,4R,5R,6aS)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4) → (3aR,4R,5R,6aS)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol (86021-78-5,105455-57-0,105455-58-1,118919-53-2,118919-54-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)86203-7

upstream raw materials:

(3aS,5S,6aR)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one

Toluene-4-sulfonic acid (3aS,5S,6aR)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester

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

thiophenol

Downstream raw materials:

(3aR,5R,6aS)-2-Methoxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-5-ol

4β-(benzenesulphonylmethyl)-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

4β-(thiophenoxymethyl)-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

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