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

Base Information

Chemical Name:Acetic acid (3R,4R,5R,6S)-2-benzyloxy-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:251361-16-7
Molecular Formula:C₁₆H₂₂O₆
Molecular Weight:310.347
Hs Code.:

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

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Chemical Property of Acetic acid (3R,4R,5R,6S)-2-benzyloxy-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (3R,4R,5R,6S)-2-benzyloxy-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (3R,4R,5R,6S)-2-benzyloxy-4-hydroxy-5-methoxy-6-methyl-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: 78.0%

: 1445-45-0
Trimethyl orthoacetate

: 251361-15-6
(3R,4S,5R,6S)-2-Benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-3,4-diol

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

Guidance literature:: Trimethyl orthoacetate; (3R,4S,5R,6S)-2-Benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-3,4-diol; With toluene-4-sulfonic acid; In acetonitrile;

With acetic acid; at 20 ℃;
DOI:10.1016/S0960-894X(99)00493-X

Reference yield:

: 73-34-7
L-rhamnose

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

Guidance literature:: Multi-step reaction with 5 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

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;
DOI:10.1016/S0960-894X(99)00493-X

Reference yield:

: 251361-11-2
benzyl L-rhamnopyranoside

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

Guidance literature:: Multi-step reaction with 4 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

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;
DOI:10.1016/S0960-894X(99)00493-X