3AR,5R,6S,7R,7AR-5-Hydroxymethyl-2-methyl-5,6,7,7A-tetrahydro-3AH-pyrano[3,2-D]thiazole-6,7-diol

Base Information

• Chemical Name: 3AR,5R,6S,7R,7AR-5-Hydroxymethyl-2-methyl-5,6,7,7A-tetrahydro-3AH-pyrano[3,2-D]thiazole-6,7-diol
• CAS No.: 179030-22-9
• Molecular Formula: C8H13NO4S
• Molecular Weight: 219.262
• UNII: ML5FHL557A
• Nikkaji Number: J760.469F
• Wikidata: Q27284100
• Pharos Ligand ID: MBRKC1KZKW64
• Metabolomics Workbench ID: 148238
• ChEMBL ID: CHEMBL257158
• Mol file: 179030-22-9.mol

Synonyms:N-acetyl-glucosamine thiazoline;N-acetylglucosamine thiazoline;NAG-thiazoline

Chemical Property of 3AR,5R,6S,7R,7AR-5-Hydroxymethyl-2-methyl-5,6,7,7A-tetrahydro-3AH-pyrano[3,2-D]thiazole-6,7-diol

Chemical Property:

• Boiling Point: 443.0±45.0 °C(Predicted)
• PKA: 13.16±0.70(Predicted)
• PSA: 107.58000
• Density: 1.81±0.1 g/cm3(Predicted)
• LogP: -1.60520
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 219.05652907
• Heavy Atom Count: 14
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

3a,6,7,7a-Tetrahydro-5-(hydroxymethyl)-2-methyl-(3aR,5R,6S,7R,7aR)-5H-pyrano[3,2-d]thiazole-6,7-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2C(C(C(OC2S1)CO)O)O
• Isomeric SMILES: CC1=N[C@@H]2[C@H]([C@@H]([C@H](O[C@@H]2S1)CO)O)O
• Uses: 3a,6,7,7a-Tetrahydro-5-(hydroxymethyl)-2-methyl-(3aR,5R,6S,7R,7aR)-5H-pyrano[3,2-d]thiazole-6,7-diol, can be used in the synthesis of Hexosaminidase inhibitors, which are the new drug candidates for the therapy of osteoarthritis.

Technology Process of 3AR,5R,6S,7R,7AR-5-Hydroxymethyl-2-methyl-5,6,7,7A-tetrahydro-3AH-pyrano[3,2-D]thiazole-6,7-diol

There total 4 articles about 3AR,5R,6S,7R,7AR-5-Hydroxymethyl-2-methyl-5,6,7,7A-tetrahydro-3AH-pyrano[3,2-D]thiazole-6,7-diol 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%

C16H18F3NO8S (944070-42-2) → (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (179030-22-9)

Guidance literature:

With methanol; sodium methylate; at 0 - 20 ℃; for 1h;

DOI:10.1021/ol0706814

Reference yield: 93.0%

(3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole (67145-37-3,67109-74-4) → (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (179030-22-9)

Guidance literature:

With TEA; water; In methanol;

DOI:10.1016/S0040-4039(00)02020-7

Reference yield: 85.0%

(S)-3-azido-2-acetamidopropanal diethyl acetal (134735-75-4) → (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (179030-22-9)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.5h;

upstream raw materials:

(3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole

C₁₆H₁₈F₃NO₈S

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

(S)-3-azido-2-acetamidopropanal diethyl acetal

Downstream raw materials:

C₁₅H₁₉NO₄S

C₁₅H₁₉NO₆S₂

Refernces

• 1、 Knapp, Spencer,Abdo, Mohannad,Ajayi, Kehinde,Huhn, Richard A.,Emge, Thomas J.,Kim, Eun Ju,Hanover, John A.. "Tautomeric modification of GIcNAc-thiazoline". . p. 2321 - 2324. Retrieved 2007.
• 2、 Huang, Gangliang,Chen, Ya. "Solid-phase synthesis of Di-N-Acetyl-β-chitobiosyl NAG-thiazoline". scheme or table. p. 649 - 651. Retrieved 2012/05/20.