2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid

Base Information

• Chemical Name: 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid
• CAS No.: 532959-22-1
• Molecular Formula: C₃₅H₃₆O₇
• Molecular Weight: 568.667

Synonyms:2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid

Chemical Property of 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid

Chemical Property:

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Technology Process of 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid

There total 3 articles about 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid 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: 90.0%

2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester (532959-21-0) → 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid (532959-22-1)

Guidance literature:

With ammonium acetate; hydrogen; palladium on activated charcoal; In methanol; for 1h;

DOI:10.1002/anie.200390139

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid (532959-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / PPh₃*HBr / 1 h / 0 - 40 °C

2: 90 percent / H₂; NH₄OAc / Pd/C / methanol / 1 h

With ammonium acetate; hydrogen; triphenylphosphine hydrobromide; palladium on activated charcoal; In methanol;

DOI:10.1002/anie.200390139

Reference yield:

2-(hydroxymethyl)benzoic acid benzyl ester (365534-57-2) → 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid (532959-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / PPh₃*HBr / 1 h / 0 - 40 °C

2: 90 percent / H₂; NH₄OAc / Pd/C / methanol / 1 h

With ammonium acetate; hydrogen; triphenylphosphine hydrobromide; palladium on activated charcoal; In methanol;

DOI:10.1002/anie.200390139

upstream raw materials:

2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester

3,4,6-tri-O-benzyl-D-glucal

2-(hydroxymethyl)benzoic acid benzyl ester

Downstream raw materials:

methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)-α-D-glucopyranoside

O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

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