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

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one
• CAS No.: 86021-69-4
• Molecular Formula: C₁₄H₁₆O₃S
• Molecular Weight: 264.345

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 6 articles about (3aR,4R,5R,6aS)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-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: 98.0%

Toluene-4-sulfonic acid (3aS,5S,6aR)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester (105394-12-5,118919-51-0) + thiophenol (108-98-5) → (3aS,5S,6aR)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4,91739-11-6,118919-52-1)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 0.5h; Ambient temperature;

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

Reference yield:

(3aR,5R,6aS)-5-Hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one (32233-40-2,54423-47-1,62561-61-9,72777-79-8,76704-05-7) → (3aS,5S,6aR)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4,91739-11-6,118919-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine / 24 h / -18 °C

2: 98 percent / t-BuOK / dimethylsulfoxide / 0.5 h / Ambient temperature

With potassium tert-butylate; In pyridine; dimethyl sulfoxide;

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

Reference yield:

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) → (3aR,4R,5R,6aS)-5-Hydroxy-4-phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2-one (86021-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 48 h / -18 °C

2: 1) t-BuOK / 1) DMSO, RT, 2) DMSO, 30 min

With pyridine; potassium tert-butylate;

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

upstream raw materials:

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

thiophenol

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

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

Downstream raw materials:

(3aS,5S,6aR)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol

(3aR,4R,5R,6aS)-4-Phenylsulfanylmethyl-hexahydro-cyclopenta[b]furan-2,5-diol

4β-(thiophenoxymethyl)-2ξ,5α-dihydroxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran-2-one

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

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