Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 208758-71-8
• Molecular Formula: C₄₂H₅₀O₁₅
• Molecular Weight: 794.85

Synonyms:

Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-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: 18.4%

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) + acetic anhydride (108-24-7) + acetobromomannose (13242-53-0) → Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (208758-71-8) + methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-benzyl-α-D-mannopyranoside (208765-55-3)

Guidance literature:

With pyridine; 4 A molecular sieve; sodium methylate; mercury dibromide; Yield given. Multistep reaction; 1) CH₂Cl₂, 24 h; 2) MeOH, pH 8, rt, overnight; 3) rt, 4 h;

DOI:10.1080/07328309808002903

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) + C17H23BrO10 → Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (208758-71-8)

Guidance literature:

C₁₇H₂₃BrO₁₀; With trifluorormethanesulfonic acid; In tetrachloromethane; dichloromethane; at -40 ℃; for 0.166667h;

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside; In tetrachloromethane; dichloromethane; at -40 - 0 ℃; for 2h;

DOI:10.1039/c7cc07332a

Reference yield:

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside (96996-90-6) → Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (208758-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanesulfonic acid / neat (no solvent) / 1 h / 90 °C

1.2: 255 / 1 h / 110 °C

2.1: sodium methylate; methanol / dichloromethane / 2 h / 20 °C / pH 9 - 10

3.1: pyridine / 2 h / 20 °C

With pyridine; methanol; methanesulfonic acid; sodium methylate; In dichloromethane;

DOI:10.1002/ejoc.202101121

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

acetobromomannose

acetic anhydride

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside

Downstream raw materials:

2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl-(1→6)-1,2,3,4-tetra-O-acetyl-α-D-mannopyranose

methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-α-D-mannopyranosyl-α-D-mannopyranoside

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