Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 114827-97-3
• Molecular Formula: C₃₁H₄₀O₁₁
• Molecular Weight: 588.652

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 9 articles about Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-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: 6.0%

methyl 4-O-benzyl-6-deoxy-α-D-glucopyranoside (131589-92-9) + Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester (106711-52-8) → Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (114827-97-3) + methyl 4-O-benzyl-6-deoxy-2-O-(2,4-di-O-acetyl-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside (131589-91-8) + Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3S,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester + Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3S,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 55 ℃;

DOI:10.1039/c39870001026

Reference yield: 4.4%

Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester (106711-52-8) + methyl 4-O-benzyl-6-deoxy-α-D-glucopyranoside (131589-92-9) → Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (114827-97-3) + methyl 4-O-benzyl-6-deoxy-2-O-(2,4-di-O-acetyl-3-O-benzyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside (131589-91-8) + Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2R,3R,4R,5R,6S)-3-benzyloxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (114827-99-5) + Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2R,3R,4R,5R,6S)-3-benzyloxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (114827-98-4)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In nitromethane; benzene; at 55 ℃; for 1h; Yields of byproduct given;

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside (131589-93-0) → Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (114827-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu3SnH, 2.) NaOMe, MeOH / 1.) α,α'-azobis-isobutyronitrile / 1.) C6H6, reflux, 2 h, 2.) pH 9, room temperature, 2 h

2: 6 percent / mercury(II) cyanide / benzene; nitromethane / 55 °C

With methanol; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; azobisisobutyronitrile; In nitromethane; benzene;

DOI:10.1039/c39870001026

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

methyl 4-O-benzyl-6-deoxy-α-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

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