1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose

Base Information

• Chemical Name: 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose
• CAS No.: 850220-29-0
• Molecular Formula: C₃₀H₃₂O₈
• Molecular Weight: 520.579
• Mol file: 850220-29-0.mol

Synonyms:1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose

Chemical Property of 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose

There total 4 articles about 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-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: 90.0%

2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol (153153-30-1) → 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (850220-29-0)

Guidance literature:

With ozone; triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.carres.2005.01.008

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (850220-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / POCl₃ / 4 h / 20 °C

2: 76 percent / NaBH₄ / methanol / 16 h / 20 °C

3: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

4: 90 percent / O₃; PPh₃ / CH₂Cl₂ / -78 - 20 °C

With dmap; sodium tetrahydroborate; ozone; triethylamine; triphenylphosphine; trichlorophosphate; In methanol; dichloromethane;

DOI:10.1016/j.carres.2005.01.008

Reference yield:

(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde (136883-91-5) → 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (850220-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / NaBH₄ / methanol / 16 h / 20 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

3: 90 percent / O₃; PPh₃ / CH₂Cl₂ / -78 - 20 °C

With dmap; sodium tetrahydroborate; ozone; triethylamine; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1016/j.carres.2005.01.008

upstream raw materials:

2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

3,4,6-tri-O-benzyl-D-glucal

(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Downstream raw materials:

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose

tri-O-benzyl-D-arabinolactone