Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
• CAS No.: 127766-51-2
• Molecular Formula: C₂₃H₂₄F₃NO₆
• Molecular Weight: 467.442

Synonyms:Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-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: 82.0%

N-((2R,3S,4S,6S)-2-Benzyloxymethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl)-2,2,2-trifluoro-acetamide (127766-50-1) → Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (127766-51-2)

Guidance literature:

benzoylation;

DOI:10.1016/S0040-4039(01)89006-7

Reference yield:

methyl 4,6-O-benzylidene-3-trifluoroacetamido-2,3-dideoxy-α-D-ribo-hexopyranoside (127853-68-3) → Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (127766-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃SiH/TiCl₄ / 0.5 h / -70 °C

2: 82 percent / benzoylation

With triethylsilane; titanium tetrachloride;

DOI:10.1016/S0040-4039(01)89006-7

Reference yield: 98.0%

Benzoic acid (2R,3S,4S,6S)-2-benzyloxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (127766-51-2) → Benzoic acid (2R,3S,4S,6S)-2-hydroxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (127766-52-3)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(01)89006-7

upstream raw materials:

N-((2R,3S,4S,6S)-2-Benzyloxymethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl)-2,2,2-trifluoro-acetamide

methyl 4,6-O-benzylidene-3-trifluoroacetamido-2,3-dideoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

Benzoic acid (2R,3S,4S,6S)-2-hydroxymethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,4S)-2-hydroxymethyl-6-oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

(2S,3S,4S,6S)-3-Benzoyloxy-6-hydroxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S)-3-Benzoyloxy-6-oxo-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

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