Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 613230-05-0
• Molecular Formula: C₂₆H₃₂O₁₃
• Molecular Weight: 552.532

Synonyms:Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl 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:

5-(4-nitro-benzenesulfonyloxy)-5-oxo-pentanoic acid benzyl ester + 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (13100-46-4) → Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester (613230-05-0)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1055/s-2003-39404

Reference yield:

glutaric acid monobenzyl ester (54322-10-0) → Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester (613230-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran / 2 h / 20 °C

2: 4.81 g / DMAP; Et₃N / tetrahydrofuran / 18 h / 20 °C

With dmap; triethylamine; In tetrahydrofuran;

DOI:10.1055/s-2003-39404

Reference yield: 76.0%

4-(3-benzyloxy-propyl)-phenol (613230-03-8) + Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-ylmethyl ester (613230-05-0) → Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[4-(3-benzyloxy-propyl)-phenoxy]-tetrahydro-pyran-2-ylmethyl ester (613230-07-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1055/s-2003-39404

upstream raw materials:

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose

glutaric acid monobenzyl ester

Downstream raw materials:

Pentanedioic acid benzyl ester (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[4-(3-benzyloxy-propyl)-phenoxy]-tetrahydro-pyran-2-ylmethyl ester

Pentanedioic acid mono-{(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[4-(3-hydroxy-propyl)-phenoxy]-tetrahydro-pyran-2-ylmethyl} ester

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