(5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione

Base Information

• Chemical Name: (5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione
• CAS No.: 72744-67-3
• Molecular Formula: C₈H₁₀N₂O₂S₂
• Molecular Weight: 230.312
• UNII: XB7LEY5M69
• ChEMBL ID: CHEMBL4459765
• Mol file: 72744-67-3.mol

Synonyms:(5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione;72744-67-3;(3R,9R)-5,11-Dithia-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione;XB7LEY5M69;CHEMBL4459765;3H,5H,8H,10H-Bisthiazolo[3,4-a:3',4'-d]pyrazine-5,10-dione, tetrahydro-, (5aR,10aR)-;(3R,9R)-5,11-dithia-1,7-diazatricyclo[7.3.0.0(3),]dodecane-2,8-dione;(3R,9R)-5,11-dithia-1,7-diazatricyclo[7.3.0.0,dodecane-2,8-dione;(5aR,10aR)-Tetrahydro-3H,5H,8H,10H-bisthiazolo[3,4-a:3',4'-d]pyrazine-5,10-dione;3H,5H,8H,10H-Bisthiazolo[3,4-a:3',4'-d]pyrazine-5,10-dione, tetrahydro-, (5aR-cis)-;5,11-Bisthio-(R,R)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,8-diketone;Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione, (5aR,10aR)-

Chemical Property of (5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione

Chemical Property:

• PSA: 108.29000
• Density: 1.62
• LogP: -0.15870
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated), Dichloromethane
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 230.01836991
• Heavy Atom Count: 14
• Complexity: 280

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

(5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3'',4''-d]pyrazine-5,10(3H,8H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(=O)N3CSCC3C(=O)N2CS1
• Isomeric SMILES: C1[C@H]2C(=O)N3CSC[C@H]3C(=O)N2CS1
• Uses: (5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3'',4''-d]pyrazine-5,10(3H,8H)-dione is a cyclic dipeptides that have anti-biofilm activity against oral pathogens. Pidotimod Impurity

Technology Process of (5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione

There total 4 articles about (5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione 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: 70.0%

(R)-thiazolidine-4-carboxylic acid hydrochloride (67089-84-3) → (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione (72744-67-3)

Guidance literature:

(R)-thiazolidine-4-carboxylic acid hydrochloride; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.06.108

Reference yield: 65.0%

L-thioproline (34592-47-7,2756-91-4,6070-92-4,60731-25-1) → (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione (72744-67-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/zaac.201300071

Reference yield:

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid (51077-16-8) → (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione (72744-67-3)

Guidance literature:

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid; With benzotriazol-1-ol; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃;

With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 3h;

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid; Further stages;

DOI:10.1080/10610278.2016.1236197

upstream raw materials:

L-thioproline

ethyl (4R)-1,3-thiazolidine-4-carboxylate

(R)-thiazolidine-4-carboxylic acid hydrochloride

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid