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

Base Information

• Chemical Name: Acetic acid (3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl ester
• CAS No.: 197087-06-2
• Molecular Formula: C₂₉H₂₉Cl₃O₆
• Molecular Weight: 579.905

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about Acetic acid (3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-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:

1-Chloro-4-(chloromethyl)benzene (104-83-6) → Acetic acid (3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl ester (197087-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NaH, Bu₄NI / dimethylformamide

2: AcOH, 3.0 M H₂SO₄ / 85 °C

3: Et₃N / CH₂Cl₂

With sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01670-5

Reference yield:

β-methyl 2,3,4-tri-O-(4-chlorobenzyl)-6-deoxy-L-galactopyranoside (152554-45-5) → Acetic acid (3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl ester (197087-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: AcOH, 3.0 M H₂SO₄ / 85 °C

2: Et₃N / CH₂Cl₂

With sulfuric acid; acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(97)01670-5

Reference yield:

methyl L-fucopyranoside (14687-15-1) → Acetic acid (3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl ester (197087-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NaH, Bu₄NI / dimethylformamide

2: AcOH, 3.0 M H₂SO₄ / 85 °C

3: Et₃N / CH₂Cl₂

With sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01670-5

upstream raw materials:

acetic anhydride

1-Chloro-4-(chloromethyl)benzene

β-methyl 2,3,4-tri-O-(4-chlorobenzyl)-6-deoxy-L-galactopyranoside

methyl L-fucopyranoside

Downstream raw materials:

2-{(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-2-phenyl-8-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-isoindole-1,3-dione

2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

C₆₅H₆₈Cl₃NO₂₀

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