8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one

Base Information

• Chemical Name: 8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one
• CAS No.: 227458-60-8
• Molecular Formula: C₈H₁₂N₂O₆S
• Molecular Weight: 264.259
• Nikkaji Number: J1.110.900D
• Wikidata: Q76280681
• Metabolomics Workbench ID: 147510
• ChEMBL ID: CHEMBL489798
• Mol file: 227458-60-8.mol

Synonyms:8,9,10-TRIHYDROXY-7-HYDROXYMETHYL-2-THIOXO-6-OXA-1,3-DIAZA-SPIRO[4.5]DECAN-4-ONE;227458-60-8;CHEMBL489798;(5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decan-4-one;(5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-2-sulfanylidene-6-oxa-1,3-diazaspiro[4.5]decan-4-one;1hlf;(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione;GL4;BDBM50263769;DB02964;PD059744;W-201947;1beta,1-(Iminocarbonothioyliminocarbonyl)-1-deoxy-D-glucopyranose;(5S,7R,8S,9S,10R)-8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one

Chemical Property of 8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one

Chemical Property:

• PSA: 163.37000
• LogP: -3.18160
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 264.04160728
• Heavy Atom Count: 17
• Complexity: 366

Purity/Quality:

95% ^*data from raw suppliers

(2R-3S-4S-5R-6S)-3-4-5-Trihydroxy-2-hydroxymethyl-7-9-diaza-1-oxa-spiro[4-5]decane-10-one-8-thione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C2(O1)C(=O)NC(=S)N2)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@]2(O1)C(=O)NC(=S)N2)O)O)O)O

Technology Process of 8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one

There total 8 articles about 8,9,10-Trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one 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: 92.0%

(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-2-benzoyloxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione (286369-08-2) → (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione (227458-60-8,189633-62-3)

Guidance literature:

With methanol; sodium methylate; Heating;

DOI:10.1016/S0957-4166(99)00486-3

Reference yield: 78.0%

(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione (227458-59-5) → (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione (227458-60-8,189633-62-3)

Guidance literature:

With sodium methylate; Ambient temperature;

DOI:10.1016/S0960-894X(99)00192-4

Reference yield:

2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide (82469-74-7) → (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione (227458-60-8,189633-62-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / TiCl₄; aq. AcOH / 144 h / 20 °C

2: 79 percent / S₈ / nitromethane / 4 h / 80 °C

3: 78 percent / NaOMe; MeOH / 20 °C

With methanol; sulfur; sodium methylate; titanium tetrachloride; acetic acid; In nitromethane;

DOI:10.1021/jm010892t

upstream raw materials:

(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione

(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-2-benzoyloxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione

2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide

C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranosyl)formamide