Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 78355-26-7
• Molecular Formula: C₃₅H₄₁NO₁₅
• Molecular Weight: 715.708
• Mol file: 78355-26-7.mol

Synonyms:Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester 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: 68.0%

2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (78355-21-2) + 3,4-di-O-Benzyl-1,6-anhydro-β-L-gulopyranose (67965-18-8) → 1,6-anhydro-3,4-di-O-benzyl-2-O-<2,4,6-tri-O-acetyl-3-O-(acetylcarbamoyl)-α-D-mannopyranosyl>-β-L-gulopyranose (78355-26-7)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1021/jo00365a013

Reference yield: 68.0%

2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide (78355-21-2) + 3,4-di-O-Benzyl-1,6-anhydro-β-L-gulopyranose (67965-18-8) → Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester (78355-26-7)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea;

DOI:10.1021/jo00331a048

Reference yield:

Methyl 2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranoside (25217-95-2) → Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((1S,2R,3S,4S,5S)-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yloxy)-tetrahydro-pyran-3-yl ester (78355-26-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂SO₄ / 24 h / 25 °C

2: 89 percent / HBr / acetic acid

3: 68 percent / CF₃SO₃Ag, (CH₃)2NCON(CH₃)2

With sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; tetramethylurea; In acetic acid;

DOI:10.1021/jo00331a048

upstream raw materials:

2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl bromide

3,4-di-O-Benzyl-1,6-anhydro-β-L-gulopyranose

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

1,2,4,6-tetra-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranose

Downstream raw materials:

1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-<2,4,6-tri-O-acetyl-3-O-(acetylcarbamoyl)-α-D-mannopyranosyl>-α-L-gulopyranose

2-O-[2,4,6-tri-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranosyl]-3,4-di-O-benzyl-6-O-acetyl-L-gulopyranosyl acetate