2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester

Base Information

• Chemical Name: 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester
• CAS No.: 883742-14-1
• Molecular Formula: C₃₅H₃₆O₈
• Molecular Weight: 584.666

Synonyms:2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester

Chemical Property of 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester

There total 3 articles about 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl 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: 95.0%

6-Allyloxy-2-hydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester (883742-13-0) → 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester (883742-14-1)

Guidance literature:

With formic acid; triethylamine; triphenylphosphine; palladium diacetate; In 1,4-dioxane; at 0 ℃;

DOI:10.1055/s-2006-932463

Reference yield:

2-allyloxy-6-hydroxybenzoic acid methyl ester (74292-73-2) → 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester (883742-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Sc(OTf)3; Drierite(R) / 1,2-dichloro-ethane / -30 - 5 °C

2: 95 percent / HCO₂H; Et₃N; PPh₃ / Pd(OAc)2 / dioxane / 0 °C

With calcium sulfate; formic acid; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate); palladium diacetate; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1055/s-2006-932463

Reference yield:

1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose (151909-89-6) → 2,6-Dihydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester (883742-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Sc(OTf)3; Drierite(R) / 1,2-dichloro-ethane / -30 - 5 °C

2: 95 percent / HCO₂H; Et₃N; PPh₃ / Pd(OAc)2 / dioxane / 0 °C

With calcium sulfate; formic acid; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate); palladium diacetate; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1055/s-2006-932463

upstream raw materials:

6-Allyloxy-2-hydroxy-3-((2R,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester

2-allyloxy-6-hydroxybenzoic acid methyl ester

1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose

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