1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose

Base Information

• Chemical Name: 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose
• CAS No.: 857419-75-1
• Molecular Formula: C₃₀H₃₂O₅
• Molecular Weight: 472.581
• Mol file: 857419-75-1.mol

Synonyms:1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose

Chemical Property of 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose

There total 7 articles about 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose 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: 81.0%

Methanesulfonic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2-oxo-propyl)-tetrahydro-pyran-3-yl ester → 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose (857419-75-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1021/ol0486627

Reference yield: 81.0%

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone (857419-66-0) → 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose (857419-75-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1021/jo0502854

Reference yield:

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene (767340-70-5) → 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose (857419-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine / 24 h / 0 °C

2: 75 percent / Jones reagent; Hg(OAc)2 / acetone; H₂O / 3 h / 0 °C

3: 81 percent / K₂CO₃ / methanol / 20 °C

With pyridine; jones reagent; mercury(II) diacetate; potassium carbonate; In methanol; water; acetone;

DOI:10.1021/jo0502854

upstream raw materials:

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene

3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-propene

2-C-(3,4,6-tri-O-benzyl-2-O-tosyl-α-D-mannopyranosyl)acetaldehyde

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-galactopyranosyl)-α-D-glucopyranoside

1,2;3,4-di-O-isopropylidene-6-thio-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-glucopyranosyl)-α-D-galactopyranoside

(3β)-cholest-5-en-3-yl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-β-D-glucopyranosyl)-N-benzyloxycarbonyl-L-threonine methyl ester