5-(d)-menthyloxy-4-phenylthiobutyrolactone

Base Information

• Chemical Name: 5-(d)-menthyloxy-4-phenylthiobutyrolactone
• CAS No.: 122169-83-9
• Molecular Formula: C₂₀H₂₈O₃S
• Molecular Weight: 348.507
• Mol file: 122169-83-9.mol

Synonyms:5-(d)-menthyloxy-4-phenylthiobutyrolactone

Chemical Property of 5-(d)-menthyloxy-4-phenylthiobutyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(d)-menthyloxy-4-phenylthiobutyrolactone

There total 3 articles about 5-(d)-menthyloxy-4-phenylthiobutyrolactone 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: 100.0%

(5S)-(D-menthyloxy)-2(5H)-furanone (122079-41-8) + thiophenol (108-98-5) → 5-(d)-menthyloxy-4-phenylthiobutyrolactone (122169-83-9)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/0040-4039(91)80582-Q

Reference yield:

(1S,2R,5S)-(+)-menthol (15356-60-2) → 5-(d)-menthyloxy-4-phenylthiobutyrolactone (122169-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 °C

2: 100 percent / triethylamine / CH₂Cl₂

With triethylamine; In dichloromethane;

Reference yield:

(-)-(5R)-5-((-)-menthyl)oxy-2<5H>-furanone (122079-45-2) → 5-(d)-menthyloxy-4-phenylthiobutyrolactone (122169-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / benzene / 1 h / Heating

2: triethylamine / CH₂Cl₂ / Ambient temperature; 0 deg C, 15 min then 20 deg C, 1 h

With triethylamine; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)86092-0

upstream raw materials:

(5S)-(D-menthyloxy)-2(5H)-furanone

thiophenol

(1S,2R,5S)-(+)-menthol

(-)-(5R)-5-((-)-menthyl)oxy-2<5H>-furanone

Downstream raw materials:

(5R)-5-(d-Menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone

(3S,3aR,7aS)-3a-Benzenesulfonyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

(5S)-5-(d-Menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone

(1S,2S,5S,6R,7R)-6-Benzenesulfonyl-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Refernces

• 1、 Jong, Johannes C. de,Berg, Keimpe J. van den,Leusen, Albert M. van,Feringa, Ben L.. "Phenylsulfonyl-substituted 5-Alkoxy-2(5H)-furanones; a New Class of Highly Reactive Chiral Dienophies.". . p. 7751 - 7754. Retrieved 2007/10/02.