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![China Supplier 4H-Thieno[2,3-b]thiopyran-4-one,5,6-dihydro-6-methyl-, 7,7-dioxide, (6S) CAS 148719-91-9 for sale](/uploads/image/20250628/4H-Thieno[2,3-b]thiopyran-4-one,5,6-dihydro-6-methyl-,_7,7-dioxide,_(6S)主图.jpg "China Supplier 4H-Thieno[2,3-b]thiopyran-4-one,5,6-dihydro-6-methyl-, 7,7-dioxide, (6S) CAS 148719-91-9 wholesale")
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Key Intermediate for Dorzolamide:
This chiral compound (CAS 130693-82-2) is a critical synthon exclusively used to manufacture dorzolamide—a prescription drug for glaucoma. Its structure features:
A bicyclic thienothiopyran core with two sulfone groups (*7,7-dioxide*).
A ketone at C4 and methyl group at C6.
(6S)-stereochemistry: Essential for biological activity.
Chemical Role:
The C4 ketone undergoes stereoselective reductive amination with ethylamine, directly forming dorzolamide’s active pharmacophore. No other significant applications exist. Handled as a solid under controlled conditions to preserve chirality.
The compound 4H-Thieno[2,3-b]thiopyran-4-one, 5,6-dihydro-6-methyl-, 7,7-dioxide, (6S) is a key chiral intermediate in the synthesis of dorzolamide (a carbonic anhydrase inhibitor used to treat glaucoma). Here's a concise breakdown:
Core Skeleton:
Bicyclic system: Thieno[2,3-b]thiopyran (fusion of thiophene + thiopyran rings).
7,7-Dioxide: Both sulfur atoms oxidized to sulfones (critical for bioactivity).
5,6-Dihydro: Partial saturation at the 5-6 bond.
4-one: Ketone at position 4.
6-Methyl: Methyl group at C6.
(6S): Chiral center with S-configuration at C6 (essential for drug efficacy).
Systematic Name:
*(6S)-5,6-Dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one 7,7-dioxide*
CAS Registry: 130693-82-2 (specific to the (6S)-enantiomer).
Synthesis of Dorzolamide:
This compound is the immediate precursor to dorzolamide’s core structure. In the final steps:
*(4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide*.
The ketone (C4=O) undergoes reductive amination with ethylamine.
Introduces the ethylamino group (–NHCH₂CH₃) at C4.
Yields dorzolamide’s active pharmacophore:
Chiral Purity: The (6S)-configuration must be preserved to match dorzolamide’s stereochemistry.
Reactivity:
Ketone at C4 is highly reactive for nucleophilic addition (e.g., amines).
Sulfone groups enhance electrophilicity and binding to carbonic anhydrase.
Stability: Sensitive to epimerization at C6; requires controlled conditions (low temperature, inert atmosphere).
Handling: Typically handled as a solid (crystalline) under anhydrous conditions.
Pharmaceutical Role: Enables stereoselective production of dorzolamide, ensuring clinical efficacy.
Synthetic Challenge: Asymmetric synthesis/purification of (6S)-isomer is critical for regulatory compliance.
Patent Significance: Protected under dorzolamide manufacturing patents (e.g., Merck & Co.).
For reference:
Final Step:
This intermediate is not biologically active itself but is indispensable for constructing the therapeutic molecule.
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