Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside
• CAS No.: 139071-07-1
• Molecular Formula: C₅₆H₆₀O₁₀
• Molecular Weight: 893.086
• Mol file: 139071-07-1.mol

Synonyms:Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside

Chemical Property of Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside

There total 10 articles about Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside 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%

Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranos-1-yl)-α-D-glucopyranoside (139071-04-8) → Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside (139071-07-1)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 0.166667h;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside (139071-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) n-butyllithium / 1) THF, -90 deg C, 30 min, 2) THF, -50 deg C, 45 min

2: 73 percent / BF₃*OEt₂ / acetonitrile / 0.17 h / 0 °C

With n-butyllithium; boron trifluoride diethyl etherate; In acetonitrile;

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside (139071-07-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) dicyclohexylcarbodiimide, dimethyl sulfoxide, pyridine, CF₃CO₂H, 2) oxalic acid dihydrate / 1) Et₂O, 0 deg C, 2 h, 2) rt, 1 h

2: 1) n-butyllithium / 1) Et₂O, THF, -40 deg C, 1 h, 2) THF, -40 deg C, 30 min, then -5 deg C, 15 h

3: 1) borane-dimethylsulfide complex, 2) aq. NaOH, 30percent H₂O₂ / 1) THF, 5 deg C, 12 h, 2) 0 deg C, 1 h, then rt, 30 min

4: 1) dicyclohexylcarbodiimide, dimethyl sulfoxide, pyridine, CF₃CO₂H, 2) oxalic acid dihydrate / 1) Et₂O, 0 deg C, 2 h, 2) rt, 1 h

5: 80 percent / NEt₃ / 18 h / 60 °C

6: 82 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

7: 82 percent / PPh₃, imidazole, iodine / toluene / 1 h / 60 °C

8: 1) n-butyllithium / 1) THF, -90 deg C, 30 min, 2) THF, -50 deg C, 45 min

9: 73 percent / BF₃*OEt₂ / acetonitrile / 0.17 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dihydrogen peroxide; iodine; oxalic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In ethanol; toluene; acetonitrile;

upstream raw materials:

Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranos-1-yl)-α-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside