5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester
CAS No.:251361-17-8
Molecular Formula:C₂₂H₂₇NO₇
Molecular Weight:417.459
Hs Code.:

Synonyms:5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

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Chemical Property of 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

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Technology Process of 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

There total 7 articles about 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-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: 84.0%

: 251354-68-4
5-methyl-1H-pyrrole-2-carboxylic anhydride

: 251361-16-7
Acetic acid (3R,4R,5R,6S)-2-benzyloxy-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

: 251361-17-8
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With CoCl₂; In acetonitrile; Heating;
DOI:10.1016/S0960-894X(99)00493-X

Reference yield:

: 73-34-7
L-rhamnose

: 251361-17-8
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 82 percent / HCl(gas) / 20 °C

2.1: 96 percent / TosOH / 20 °C

3.1: 100 percent / t-BuOK / tetrahydrofuran / 20 °C

4.1: 100 percent / aq. CF₃COOH / 20 °C

5.1: TosOH / acetonitrile

5.2: 78 percent / aq. AcOH / 20 °C

6.1: 84 percent / CoCl₂ / acetonitrile / Heating

With hydrogenchloride; potassium tert-butylate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; acetonitrile; 1.1: Alkylation / 2.1: Etherification / 3.1: Methylation / 4.1: Hydrolysis / 5.1: Substitution / 5.2: Hydrolysis / 6.1: Esterification;
DOI:10.1016/S0960-894X(99)00493-X

Reference yield:

: 251361-11-2
benzyl L-rhamnopyranoside

: 251361-17-8
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4R,5S,6S)-3-acetoxy-2-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / TosOH / 20 °C

2.1: 100 percent / t-BuOK / tetrahydrofuran / 20 °C

3.1: 100 percent / aq. CF₃COOH / 20 °C

4.1: TosOH / acetonitrile

4.2: 78 percent / aq. AcOH / 20 °C

5.1: 84 percent / CoCl₂ / acetonitrile / Heating

With potassium tert-butylate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; acetonitrile; 1.1: Etherification / 2.1: Methylation / 3.1: Hydrolysis / 4.1: Substitution / 4.2: Hydrolysis / 5.1: Esterification;
DOI:10.1016/S0960-894X(99)00493-X