4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol

Base Information

• Chemical Name: 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol
• CAS No.: 909253-94-7
• Molecular Formula: C₂₇H₃₃NO₁₁
• Molecular Weight: 547.559
• Mol file: 909253-94-7.mol

Synonyms:4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol

Chemical Property of 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol

There total 5 articles about 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol 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: 100.0%

3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol (909100-00-1) → 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol (909253-94-7)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1016/j.carres.2006.05.004

Reference yield:

4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol (909099-99-6) → 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol (909253-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / 4 A MS; TMSOTf / CH₂Cl₂ / 0.25 h / cooling

2: 100 percent / NaOMe / methanol / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.carres.2006.05.004

Reference yield:

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) → 4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-3-O-β-D-glucopyranosyl-1,5-imino-D-glucitol (909253-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃

2: 71 percent / 4 A MS; TMSOTf / CH₂Cl₂ / 0.25 h / cooling

3: 100 percent / NaOMe / methanol / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; In methanol; dichloromethane;

DOI:10.1016/j.carres.2006.05.004

upstream raw materials:

3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

2,3,4,5-tetra-O-acetyl-D-glucopyranose

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate