(3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime

Base Information

• Chemical Name: (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime
• CAS No.: 787612-03-7
• Molecular Formula: C₂₀H₁₇NO₆
• Molecular Weight: 367.358
• Mol file: 787612-03-7.mol

Synonyms:(3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime

Chemical Property of (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime

There total 2 articles about (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime 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: 73.0%

1,3,4,5-tetra-O-benzoyl-2,6-anhydro-D-arabino-hex-1-(Z)-enitol (787612-01-5) → (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime (787612-03-7)

Guidance literature:

With hydroxylamine hydrochloride; In pyridine; at 60 ℃; for 24h;

DOI:10.1016/j.tetasy.2004.07.018

Reference yield:

1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide (17187-64-3) → (3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime (787612-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / 4A MS; DBU / acetonitrile / 2 h

2: 73 percent / hydroxylamine hydrochloride / pyridine / 24 h / 60 °C

With hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; acetonitrile;

DOI:10.1016/j.tetasy.2004.07.018

Reference yield: 79.0%

(3S,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran oxime (787612-03-7) + benzoyl chloride (98-88-4) → (3R,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran O-benzoyloxime

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.tetasy.2004.07.018

upstream raw materials:

1,3,4,5-tetra-O-benzoyl-2,6-anhydro-D-arabino-hex-1-(Z)-enitol

1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide

Downstream raw materials:

(3R,4S)-3,4-bis(benzoyloxy)-6-formyl-3,4-dihydro-2H-pyran