(2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide
• CAS No.: 394247-92-8
• Molecular Formula: C₃₁H₃₄ClF₆IN₄O₁₁
• Molecular Weight: 914.979

Synonyms:(2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide

Chemical Property of (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide

There total 11 articles about (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide 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:

acetic acid 3-acetoxy-2-acetoxymethyl-6-[6-carbamoyl-4-[3-(4-chloro-3-trifluoromethyl-phenyl)-ureido]-2-(2-iodo-ethoxy)-5-methoxy-tetrahydro-pyran-3-yloxy]-5-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-4-yl ester → (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide (394247-92-8)

Guidance literature:

With sodium methylate; In methanol; for 2h;

DOI:10.1021/ja0166693

Reference yield:

3-(trifluoromethyl)benzoic acid (454-92-2) → (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide (394247-92-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

2.1: 92 percent / 4-dimethylaminopyridine / pyridine / 2 h / 20 °C

3.1: 83 percent / (CF₃CO₂)2Hg; (C₂H₅)2O*BF₃ / 4.5 h

4.1: Me₃P / tetrahydrofuran; ethanol / 1.5 h

4.2: H₂O / tetrahydrofuran; ethanol / 12 h

5.1: 72 mg / CH₂Cl₂; dimethylformamide / 3.5 h

6.1: NaI / acetone / 24 h / Heating

7.1: 66 mg / NaOMe / methanol / 2 h

With dmap; boron trifluoride diethyl etherate; sodium methylate; mercury(II) trifluoroacetate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; trimethylphosphane; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja0166693

Reference yield:

4-chloro-3-(trifluoromethyl)phenyl isocyanate (327-78-6) → (2S,3S,4S,5R,6S)-4-[3-(4-Chloro-3-trifluoromethyl-phenyl)-ureido]-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-yloxy]-6-(2-iodo-ethoxy)-3-methoxy-tetrahydro-pyran-2-carboxylic acid amide (394247-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 mg / CH₂Cl₂; dimethylformamide / 3.5 h

2: NaI / acetone / 24 h / Heating

3: 66 mg / NaOMe / methanol / 2 h

With sodium methylate; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja0166693

upstream raw materials:

3-(trifluoromethyl)benzoic acid

4-chloro-3-(trifluoromethyl)phenyl isocyanate

phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

phenyl 2-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Downstream raw materials:

C₁₀₀H₁₀₅Cl₃F₆N₁₂O₃₀

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