3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose

Base Information

• Chemical Name: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose
• CAS No.: 211800-60-1
• Molecular Formula: C₁₀H₁₂O₆
• Molecular Weight: 228.202
• Mol file: 211800-60-1.mol

Synonyms:3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose

Chemical Property of 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose

There total 2 articles about 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose 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%

acetic anhydride (108-24-7) + 1,5-D-anhydrofructose (75414-43-6) → 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose (211800-60-1)

Guidance literature:

1,5-D-anhydrofructose; With water; at 20 ℃; for 24h;

acetic anhydride; With pyridine; at 25 ℃; for 9h;

DOI:10.1016/j.carres.2004.06.007

Reference yield: 45.0%

acetic anhydride (108-24-7) + 1,5-D-anhydrofructose (75414-43-6) → 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose (211800-60-1) + ((2R,3R,4S,5S)-3,4-diacetoxy-2-acetoxymethyl-tetrahydropyran)-5-spiro-5'-((1'R,2'R,3'S,7'R)-2',7'-diacetoxy-1'-acetoxymethyl-4',6',9'-trioxabicyclo[4,3,0]nonane) + ((2R,3R,4S,5S)-3,4-diacetoxy-2-acetoxymethyl-tetrahydropyran)-5-spiro-5'-((1'R,2'R,3'S,7'S)-2',7'-diacetoxy-1'-acetoxymethyl-4',6',9'-trioxabicyclo[4,3,0]nonane)

Guidance literature:

With pyridine; at 5 ℃; Yields of byproduct given;

DOI:10.1016/S0008-6215(98)00058-5

Reference yield: 59.0%

3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose (211800-60-1) → 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (68733-00-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16.5h;

DOI:10.1016/j.carres.2006.03.037

upstream raw materials:

acetic anhydride

1,5-D-anhydrofructose

Downstream raw materials:

1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose

1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulose

2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose