1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol

Base Information

• Chemical Name: 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol
• CAS No.: 203862-58-2
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 203862-58-2.mol

Synonyms:1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol

Chemical Property of 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol

There total 4 articles about 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol 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: 83.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran (3971-47-9,7103-29-9,13035-11-5,26242-03-5) → 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol (203862-58-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1139/v93-239

Reference yield:

D-arabino-1,5-anhydro-2-deoxy-hexitol + p-Anisaldehyde dimethyl acetal (2186-92-7) → hexane (110-54-3) + 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol (203862-58-2)

Guidance literature:

With triethylamine; toluene-4-sulfonic acid; In 2,4-dichlorophenoxyacetic acid dimethylamine; ethyl acetate;

Reference yield:

3,4,6-tri-O-acetyl-1,2-dideoxy-D-glucopyranose (13035-12-6,53269-94-6,53735-78-7) → 1,5-anhydro-2-deoxy-4,6-O-p-methoxybenzylidene-D-arabino-hexitol (203862-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; methanol / 9 h / 20 °C / Inert atmosphere

2: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With methanol; camphor-10-sulfonic acid; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/ol401367h

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

D-glucal triacetate

3,4,6-tri-O-acetyl-1,2-dideoxy-D-glucopyranose

Downstream raw materials:

C₂₇H₄₀O₄Si

C₂₆H₃₈O₅Si

C₄₄H₇₅NO₇Si₂

C₄₅H₇₇O₉PSi₂