1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose

Base Information

• Chemical Name: 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose
• CAS No.: 102871-17-0
• Molecular Formula: C₃₇H₄₅NO₁₇
• Molecular Weight: 775.761
• Mol file: 102871-17-0.mol

Synonyms:1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose

Chemical Property of 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose

There total 5 articles about 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-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: 86.0%

1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (99605-12-6) + Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-carbamoyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (217180-21-7) → 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose (102871-16-9,102871-17-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/ja9819458

Reference yield:

2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranoside (162112-03-0) → 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose (102871-16-9,102871-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / K₂CO₃

2: 86 percent / BF₃*OEt₂ / CH₂Cl₂

With boron trifluoride diethyl etherate; potassium carbonate; In dichloromethane;

DOI:10.1021/ja9819458

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose (99748-10-4) → 1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose (102871-16-9,102871-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / NH₃

2: 97 percent / K₂CO₃

3: 86 percent / BF₃*OEt₂ / CH₂Cl₂

With boron trifluoride diethyl etherate; ammonia; potassium carbonate; In dichloromethane;

DOI:10.1021/ja9819458

upstream raw materials:

1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose

Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-carbamoyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranoside

1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose

Downstream raw materials:

1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-L-gulopyranose

1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-L-gulopyranose

6-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α/β-gulopyranoside

Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester