di-O-acetyl-1,4;3,6-dianhydro-L-iditol

Base Information

• Chemical Name: di-O-acetyl-1,4;3,6-dianhydro-L-iditol
• CAS No.: 24808-18-2
• Molecular Formula: C₁₀H₁₄O₆
• Molecular Weight: 230.218
• Mol file: 24808-18-2.mol

Synonyms:di-O-acetyl-1,4;3,6-dianhydro-L-iditol

Chemical Property of di-O-acetyl-1,4;3,6-dianhydro-L-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-O-acetyl-1,4;3,6-dianhydro-L-iditol

There total 4 articles about di-O-acetyl-1,4;3,6-dianhydro-L-iditol 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: 84.0%

potassium acetate (127-08-2) + (3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) (54522-28-0,66966-12-9,67890-26-0,76793-35-6,107740-09-0) → di-O-acetyl-1,4;3,6-dianhydro-L-iditol (24808-18-2,54522-25-7)

Guidance literature:

In N,N-dimethyl-formamide; at 140 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.1c10278

Reference yield:

1,4:3,6-dianhydro-D-mannitol (641-74-7) → di-O-acetyl-1,4;3,6-dianhydro-L-iditol (24808-18-2,54522-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 16 h / 0 - 22 °C / Inert atmosphere; Schlenk technique

2: N,N-dimethyl-formamide / 16 h / 140 °C / Inert atmosphere; Schlenk technique

With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.1c10278

Reference yield:

(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) (54522-28-0,66966-12-9,67890-26-0,76793-35-6,107740-09-0) → di-O-acetyl-1,4;3,6-dianhydro-L-iditol (24808-18-2,54522-25-7)

Guidance literature:

With tetraethylammonium acetate; acetone;

DOI:10.1021/ja01594a055

upstream raw materials:

(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)

acetone

1,4:3,6-dianhydro-D-mannitol

potassium acetate

Downstream raw materials:

1,4:3,6-dianhydro-L-iditol

1,4:3,6-dianhydro-2,5-di-O-p-tosyl-D-iditol

Refernces