(2R,4S,5Z,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-one

Base Information

• Chemical Name: (2R,4S,5Z,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-one
• CAS No.: 127393-89-9
• Molecular Formula: C10H16 O5
• Molecular Weight: 216.231
• DSSTox Substance ID: DTXSID501017473
• Nikkaji Number: J476.831K
• Wikidata: Q105034717
• Mol file: 127393-89-9.mol

Synonyms:decarestrictine D;tuckolide

Chemical Property of (2R,4S,5Z,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-one

Chemical Property:

• Vapor Pressure: 1.07E-09mmHg at 25°C
• Melting Point: 121-123℃ (dichloromethane hexane )
• Boiling Point: 442.7°C at 760 mmHg
• PKA: 13.34±0.70(Predicted)
• Flash Point: 176.2°C
• PSA: 86.99000
• Density: 1.278g/cm³
• LogP: -0.64920
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 216.09977361
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

98% ^*data from raw suppliers

Decarestrictine D ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C=CC(C(CC(=O)O1)O)O)O
• Isomeric SMILES: C[C@@H]1C[C@@H](/C=C\[C@@H]([C@H](CC(=O)O1)O)O)O

Technology Process of (2R,4S,5Z,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-one

There total 53 articles about (2R,4S,5Z,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-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: 81.0%

(E)-(4S,5S,8S,10R)-4,5,8-Tris-methoxymethoxy-10-methyl-3,4,5,8,9,10-hexahydro-oxecin-2-one (851278-53-0) → (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (127393-89-9,147705-04-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In butan-1-ol; for 3.5h; Heating;

DOI:10.1021/ol050148t DOI:10.1021/jo0623890

Reference yield: 80.0%

(E)-(4S,5S,8S,10R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-10-methyl-3,4,5,8,9,10-hexahydro-oxecin-2-one (210647-33-9) → (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (127393-89-9,147705-04-2)

Guidance literature:

With hydrogen fluoride; tetrabutyl ammonium fluoride; In acetonitrile;

DOI:10.1016/S0040-4039(98)00837-5

Reference yield: 78.0%

(E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (1030835-90-5) → (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (127393-89-9,147705-04-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.200700868

upstream raw materials:

(3aS,7R,9S,11aS,E)-9-(methoxymethoxy)-2,2,7-trimethyl-3a,4,8,9-tetrahydro-7H-[1,3]dioxolo[4,5-d]oxecin-5(11aH)-one

(E)-(4S,5S,8S,10R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-10-methyl-3,4,5,8,9,10-hexahydro-oxecin-2-one

(E)-(4S,5S,8S,10R)-4,5,8-Tris-methoxymethoxy-10-methyl-3,4,5,8,9,10-hexahydro-oxecin-2-one

(R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene

Downstream raw materials:

Benzoic acid (2S,3S,5R,6R)-6-((E)-(2R,4S,7S,8S)-7,8-dihydroxy-2-methyl-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-4-yloxy)-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3S,5R,6S)-6-((E)-(4S,5S,8S,10R)-5,8-dihydroxy-10-methyl-2-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yloxy)-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester