D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone

Base Information

• Chemical Name: D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone
• CAS No.: 312308-51-3
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.154
• DSSTox Substance ID: DTXSID801213042
• Mol file: 312308-51-3.mol

Synonyms:D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone;DTXSID801213042;312308-51-3

Chemical Property of D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 177

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCC1C(C(C(=O)O1)O)O
• Isomeric SMILES: C=CC[C@@H]1[C@@H]([C@@H](C(=O)O1)O)O

Technology Process of D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone

There total 2 articles about D-lyxo-Hept-6-enonic acid, 5,6,7-trideoxy-, gamma-lactone 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: 91.0%

(4S,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester (312308-48-8) → (3S,4R,5R)-5-Allyl-3,4-dihydroxy-dihydro-furan-2-one (312308-51-3)

Guidance literature:

With hydrogenchloride; In methanol; at 0 ℃; for 3h;

DOI:10.1021/ol006457v

Reference yield:

(4S,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester (329077-40-9) → (3S,4R,5R)-5-Allyl-3,4-dihydroxy-dihydro-furan-2-one (312308-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; toluene / 2 h / 0 - 18 °C

2: 91 percent / HCl / methanol / 3 h / 0 °C

With hydrogenchloride; In tetrahydrofuran; methanol; toluene; 1: Wittig reaction / 2: Cyclization;

DOI:10.1021/ol006457v

Reference yield:

(3S,4R,5R)-5-Allyl-3,4-dihydroxy-dihydro-furan-2-one (312308-51-3) → (+)-aspicilin (52461-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / imidazole / dimethylformamide / 12 h / 18 °C

2.1: 1.2 g / DIBAL-H / hexane / 0.08 h / -78 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 1.40 g / tetrahydrofuran / 0.5 h / 0 °C

4.1: 70 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 14 h / 18 °C

5.1: 92 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 0.4 h / 18 °C

6.1: 76 percent / HCl / methanol / 3 h / 0 °C

With 1H-imidazole; hydrogenchloride; hydrogen; sodium hydride; diisobutylaluminium hydride; Pd-BaSO₄; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Reduction / 3.1: deprotonation / 3.2: Wadsworth-Emmons reaction / 4.1: Cyclization / 5.1: Catalytic hydrogenation / 6.1: deprotection;

DOI:10.1021/ol006457v

upstream raw materials:

(4S,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

(4S,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Downstream raw materials:

(+)-aspicilin