(4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide

Base Information

• Chemical Name: (4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide
• CAS No.: 147086-81-5
• Molecular Formula: C₈H₁₀O₃S₂
• Molecular Weight: 218.298
• European Community (EC) Number: 417-290-3,695-657-9
• UNII: JJ8MBD49UR
• DSSTox Substance ID: DTXSID3057646
• Nikkaji Number: J532.518H
• Wikidata: Q27281532
• ChEMBL ID: CHEMBL3189041
• Mol file: 147086-81-5.mol

Synonyms:147086-81-5;(4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide;(4S,6S)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-ol;UNII-JJ8MBD49UR;JJ8MBD49UR;DTXSID3057646;5,6-Dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-4-ol 7,7-dioxide, (4S,6S)-;EC 417-290-3;(4S,6S)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-4-ol 7,7-dioxide;(4S,6s)-5,6-dihydro-6-methyl-4h-thieno[2,3-b]thiopyran-4-ol 7,7-dioxide;Trans-hydroxy sulfone;(4S,6S)-5,6-Dihydro-4-hydroxy-6-methylthieno[2,3-b]thiopyran-7,7-dioxide;CHEMBL3189041;DTXCID4031435;SCHEMBL12315840;AMY8619;Tox21_113917;AKOS015898773;AC-6911;(4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran7,7-dioxide;NCGC00262921-01;TS-00482;CAS-147086-81-5;A884465;Q27281532;(3S,5S)-3-methyl-2,2-dioxo-2$l^{6},9-dithiabicyclo[4.3.0]nona-7,10-die n-5-ol;(4S)-5,6-Dihydro-4-hydroxy-6alpha-methyl-4H-thieno[2,3-b]thiopyran 7,7-dioxide;(4S,6S)-5,6-DIHYDRO-4-HYDROXY-6-METHYLTHIENO(2,3-B)THIOPYRAN 7,7-DIOXIDE;4H-THIENO(2,3-B)THIOPYRAN-4-OL, 5,6-DIHYDRO-6-METHYL-, 7,7-DIOXIDE, (4S,6S)-;4H-THIENO(2,3-B)THIOPYRAN-4-OL, 5,6-DIHYDRO-6-METHYL-, 7,7-DIOXIDE, (4S-TRANS)-

Chemical Property of (4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide

Chemical Property:

• Refractive Index: 1.66
• Boiling Point: 433.338 °C at 760 mmHg
• PKA: 13.06±0.40(Predicted)
• Flash Point: 215.876 °C
• PSA: 73.77000
• Density: 1.462 g/cm³
• LogP: 2.40090
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 218.00713652
• Heavy Atom Count: 13
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

(4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran7,7-dioxide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C2=C(S1(=O)=O)SC=C2)O
• Isomeric SMILES: C[C@H]1C[C@@H](C2=C(S1(=O)=O)SC=C2)O
• Uses: (4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-7,7-dioxide is a key intermediate used in the synthesis of topically-active carbonic anhydrase inhibitor MK-0507.

Technology Process of (4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide

There total 14 articles about (4S,6S)-4-Hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide 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%

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one 7,7-dioxide (148719-91-9) → (4R,6S)-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide (147086-81-5,147128-77-6,162490-45-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.1016/0957-4166(96)00350-3

Reference yield: 95.2%

5,6-dihydro-4-oxo-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide (894793-33-0) → 5,6-dihydro-4-hydroxy-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide (147086-81-5,147128-77-6,162490-45-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 10 - 20 ℃;

Reference yield: 87.0%

vinyl acetate (108-05-4,9003-20-7) + 4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide (147086-81-5,147128-77-6,162490-45-1) → (4S,6R)-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide (1197375-13-5,147086-81-5,147128-77-6,162490-45-1) + 5,6-dihydro-(R)-4-acetoxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide (148810-82-6)

Guidance literature:

With lipase PS-D; In acetone; toluene; at 23 - 24 ℃; for 3h; optical yield given as %ee; Resolution of racemate;

DOI:10.1002/ejoc.200900672

upstream raw materials:

5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

(S)-3-(thien-2-ylthio)butyric acid

methyl (S)-3-(thiophen-2-ylthio)butyrate

Downstream raw materials:

N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-4-yl)acetamide 7,7-dioxide

(4S,6R)-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran 7,7-dioxide

5,6-dihydro-(R)-4-acetoxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide

5,6-dihydro-4H-4-acetyl amino-6-methylthieno[2,3-b]thiopyran-7,7-dioxide

Refernces

• 1、 -. "PROCESS FOR PREPARING DORZOLAMIDE HYDROCHLORIDE AND ITS INTERMEDIATE". Page/Page column 20; 26. . Retrieved 2010/06/17.
• 2、 Turcu, Mihaela C.,Rantapaju, Maria,Kanerva, Liisa T.. "Applying lipase catalysis to access the enantiomers of dorzolamide intermediates". experimental part. p. 5594 - 5600. Retrieved 2010/03/01.