(R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate

Base Information

• Chemical Name: (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate
• CAS No.: 1403603-70-2
• Molecular Formula: C₃₉H₄₄O₈S
• Molecular Weight: 672.84

Synonyms:(R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate

Chemical Property of (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate

There total 7 articles about (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate 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: 85.0%

ethyl 6-O-benzyl-2-O-(4-methoxybenzyl)-thio-β-D-galactopyran-3,4-diol (1403603-69-9) + (S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester (146953-71-1) → (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate (1403603-70-2)

Guidance literature:

ethyl 6-O-benzyl-2-O-(4-methoxybenzyl)-thio-β-D-galactopyran-3,4-diol; With di(n-butyl)tin oxide; In methanol; for 2h; Inert atmosphere; Reflux;

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester; With cesium fluoride; In tetrahydrofuran; for 1.25h; Inert atmosphere;

DOI:10.1021/ml300263x

Reference yield:

ethyl 6-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside → (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate (1403603-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: water; acetic acid / 50 °C / Inert atmosphere

3.1: di(n-butyl)tin oxide / methanol / 2 h / Inert atmosphere; Reflux

3.2: 1.25 h / Inert atmosphere

With sodium hydride; di(n-butyl)tin oxide; In methanol; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ml300263x

Reference yield:

benzyl bromide (100-39-0) → (R)-benzyl-2-((2R,3S,4S,5R,6S)-2-(benzyloxymethyl)-6-(ethylthio)-3-hydroxy-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoate (1403603-70-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere; Reflux

3.1: pyridine; dmap / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / Inert atmosphere

5.1: sodium methylate / methanol / Inert atmosphere

6.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / Inert atmosphere

7.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

8.1: water; acetic acid / 50 °C / Inert atmosphere

9.1: di(n-butyl)tin oxide / methanol / 2 h / Inert atmosphere; Reflux

9.2: 1.25 h / Inert atmosphere

With pyridine; hydrogenchloride; dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ml300263x

upstream raw materials:

ethyl 6-O-benzyl-2-O-(4-methoxybenzyl)-thio-β-D-galactopyran-3,4-diol

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester

benzyl bromide

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

(2R,3S,4R,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-hydroxytetrhydro-2H-pyran-3-yl benzoate

(2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-2-(benzyloxymethyl)-6-(ethylthio)-5-(4-methoxybenzyloxy)tetrahydro-2H-pyran-yl benzoate

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