(2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

Base Information

• Chemical Name: (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate
• CAS No.: 1403603-65-5
• Molecular Formula: C₄₇H₅₆O₁₉
• Molecular Weight: 924.95

Synonyms:(2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

Chemical Property of (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

Chemical Property:

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Technology Process of (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

There total 3 articles about (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate 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: 60.0%

(2R,3R)-2-hydroxy-3-(3,4,5-tri-O-benzyl-α-L-fucopyranos-l-yl)-succinic acid dimethyl ester (178454-13-2) + ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55722-49-1) → (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate (1403603-65-5)

Guidance literature:

(2R,3R)-2-hydroxy-3-(3,4,5-tri-O-benzyl-α-L-fucopyranos-l-yl)-succinic acid dimethyl ester; ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside; In dichloromethane; for 4h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -30 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ml300263x

Reference yield:

benzyl bromide (100-39-0) → (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate (1403603-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: dichloromethane / 4 h / Molecular sieve; Inert atmosphere

2.2: 1 h / -30 °C / Inert atmosphere

3.1: dichloromethane / 4 h / Molecular sieve; Inert atmosphere

3.2: 1 h / -30 °C / Inert atmosphere

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ml300263x

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate (1403603-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 4 h / Molecular sieve; Inert atmosphere

1.2: 1 h / -30 °C / Inert atmosphere

2.1: dichloromethane / 4 h / Molecular sieve; Inert atmosphere

2.2: 1 h / -30 °C / Inert atmosphere

In dichloromethane;

DOI:10.1021/ml300263x

upstream raw materials:

benzyl bromide

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

(2R,3R)-2-hydroxy-3-(3,4,5-tri-O-benzyl-α-L-fucopyranos-l-yl)-succinic acid dimethyl ester

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

(2R,3R)-dimethyl 2-((2S,3R,4S,5S,6R)-5-(1-naphthoyloxy)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-3-(benzyloxycarbonyloxy)-6-(benzyloxymethyl)tetrahydro-2Hpyran-2-yloxy)-3-((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

(2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid

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