Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 78355-22-3
• Molecular Formula: C₄₉H₅₅NO₁₆
• Molecular Weight: 913.973

Synonyms:Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-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: 82.0%

1,2,4,6-tetra-O-acetyl-3-O-(N-acetylcarbamoyl)-α-D-mannopyranose (78355-20-1) + Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) → Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (78355-22-3)

Guidance literature:

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

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-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (78355-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / 24 h / 25 °C

2: 82 percent / CF₃SO₃Ag, (CH₃)2NCON(CH₃)2 / CH₂Cl₂ / 12 h / 25 °C

With sulfuric acid; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane;

DOI:10.1021/jo00331a048

Reference yield:

2-O-Acetyl-3,4,6-tri-O-benzyl-β-L-gulopyranosyl chloride (78355-27-8) → Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-acetylcarbamoyloxy-2-((3S,4S,5R,6S)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (78355-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 25 percent / CF₃SO₃Ag / CH₂Cl₂

2: 95 percent / CH₃ONa / methanol

3: 82 percent / CF₃SO₃Ag, (CH₃)2NCON(CH₃)2 / CH₂Cl₂ / 12 h / 25 °C

With sodium methylate; silver trifluoromethanesulfonate; tetramethylurea; In methanol; dichloromethane;

DOI:10.1021/jo00331a048

upstream raw materials:

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

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside

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

2-O-Acetyl-3,4,6-tri-O-benzyl-β-L-gulopyranosyl chloride

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