(6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone

Base Information

• Chemical Name: (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone
• CAS No.: 118477-21-7
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.326
• Mol file: 118477-21-7.mol

Synonyms:(6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone

Chemical Property of (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone

There total 1 articles about (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid 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: 45.0%

Isobengamide E (118477-05-7) + 2,2-dimethoxy-propane (77-76-9) → (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone (118477-21-7) + (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-3-methyl-but-1-enyl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-propionic acid (118477-19-3) + 2-aminocaprolactam (21568-87-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/ja00184a037

Reference yield: 85.0%

(6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone (118477-21-7) + 2-aminocaprolactam (21568-87-6) → bengamide E (1053711-16-2)

Guidance literature:

In isopropyl alcohol; for 18h; Heating;

DOI:10.1021/jo0017133

Reference yield:

(6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone (118477-21-7) → bengamide B (104947-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / propan-2-ol / 16 h / 80 °C

2: 73 percent / TFA / tetrahydrofuran; H₂O / 0.33 h / 0 °C

With trifluoroacetic acid; In tetrahydrofuran; water; isopropyl alcohol;

DOI:10.1021/jo0017133

upstream raw materials:

Isobengamide E

2,2-dimethoxy-propane

Downstream raw materials:

bengamide E

bengamide B