((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Base Information

• Chemical Name: ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester
• CAS No.: 613681-75-7
• Molecular Formula: C₃₃H₄₀O₇
• Molecular Weight: 548.676

Synonyms:((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Chemical Property of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

There total 2 articles about ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl 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: 79.0%

bromoacetic acid tert-butyl ester (5292-43-3) + 2,3,4-tri-O-benzyl-L-rhamnono-δ-lactone (259827-51-5) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester (613681-75-7)

Guidance literature:

With magnesium; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0957-4166(03)00533-0

Reference yield:

2,3,4-tri-O-benzyl-L-rhamnopyranose (210426-02-1) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester (613681-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium chlorochromate; molecular sieves / CH₂Cl₂

2: 79 percent / magnesium / tetrahydrofuran / 20 °C

With molecular sieve; magnesium; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(03)00533-0

Reference yield:

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester (613681-75-7) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1055/s-2004-837204

upstream raw materials:

bromoacetic acid tert-butyl ester

2,3,4-tri-O-benzyl-L-rhamnono-δ-lactone

2,3,4-tri-O-benzyl-L-rhamnopyranose

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