methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside
• CAS No.: 796873-53-5
• Molecular Formula: C₃₁H₄₁NO₁₆
• Molecular Weight: 683.664
• Mol file: 796873-53-5.mol

Synonyms:methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Chemical Property of methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

There total 10 articles about methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-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:

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (104707-00-8) → methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (796873-53-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

6: 100 percent / TFA / 12 h / 20 °C

7: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

8: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

9: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

10: NaBH₄; NiCl₂*6H₂O; B(OH)3 / ethanol / 0.5 h

11: 51.0 mg / pyridine / 12 h

With pyridine; dmap; sodium hypochlorite; sodium tetrahydroborate; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; boric acid; potassium carbonate; benzylamine; trifluoroacetic acid; potassium bromide; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; sodium hydrogencarbonate; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-D-glucopyranose → methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (796873-53-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

2: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

3: NaBH₄; NiCl₂*6H₂O; B(OH)3 / ethanol / 0.5 h

4: 51.0 mg / pyridine / 12 h

With pyridine; sodium tetrahydroborate; boron trifluoride diethyl etherate; boric acid; potassium carbonate; nickel dichloride; In ethanol; dichloromethane;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7) → methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (796873-53-5)

Guidance literature:

Multi-step reaction with 8 steps

1: dimethylformamide / 12 h

2: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

3: 100 percent / TFA / 12 h / 20 °C

4: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

5: 81 percent / K₂CO₃ / CH₂Cl₂ / 12 h / 20 °C

6: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

7: NaBH₄; NiCl₂*6H₂O; B(OH)3 / ethanol / 0.5 h

8: 51.0 mg / pyridine / 12 h

With pyridine; dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; boric acid; potassium carbonate; benzylamine; trifluoroacetic acid; nickel dichloride; In diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.07.018

upstream raw materials:

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

Downstream raw materials:

methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside