2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose

Base Information

• Chemical Name: 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose
• CAS No.: 334834-29-6
• Molecular Formula: C₄₉H₄₇NO₁₆
• Molecular Weight: 905.909
• Mol file: 334834-29-6.mol

Synonyms:2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose

Chemical Property of 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose

There total 11 articles about 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose 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: 78.0%

4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose (334834-24-1) + 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide (334834-28-5) → 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose (334834-29-6)

Guidance literature:

4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose; 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide; With 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at -15 ℃; for 1h;

With silver trifluoromethanesulfonate; In dichloromethane; at -15 - 20 ℃; Further stages.;

DOI:10.1021/ja003508a

Reference yield:

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside (81562-09-6) → 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose (334834-29-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / 0.2 N HCl / ethanol / Heating

2.1: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h

3.1: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

3.2: 72 percent / triethylsilane / CH₂Cl₂ / 1 h

4.1: pyridine

5.1: 3.66 g / pyridine / 4 h

6.1: 91 percent / NaNO₂ / hexamethylphosphoric acid triamide / 16 h / 20 °C

7.1: DBMP / CH₂Cl₂ / 1 h / -15 °C

7.2: 78 percent / AgOTf / CH₂Cl₂ / -15 - 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; sodium nitrite; In N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane;

DOI:10.1021/ja003508a

Reference yield:

1,6-anhydro-2,4-di-O-benzyl-β-D-mannopyranose (86861-42-9) → 2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose (334834-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 20 °C

2.1: 88 percent / TFA / 10 h / 20 °C

3.1: 94 percent / 30percent HBr; AcOH / 8 h

4.1: DBMP / CH₂Cl₂ / 1 h / -15 °C

4.2: 78 percent / AgOTf / CH₂Cl₂ / -15 - 20 °C

With dmap; 2,6-di-tert-butyl-4-methyl-phenol; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja003508a

upstream raw materials:

4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose

6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

1,6-anhydro-2,4-di-O-benzyl-β-D-mannopyranose