(2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran
• CAS No.: 77398-05-1
• Molecular Formula: C₁₅H₁₃F₃N₂O₆
• Molecular Weight: 374.273
• Mol file: 77398-05-1.mol

Synonyms:(2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran

Chemical Property of (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran

There total 15 articles about (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran 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: 95.0%

4-nitro-benzoyl chloride (122-04-3) + 1,5-anhydro-2,3,6-tridesoxy-3-trifluoroacetamido-D-xylo-hex-1-enitol (76793-56-1) → 1,5-anhydro-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-xylo-hex-1-enitol (72384-25-9,73891-04-0,73891-07-3,76793-53-8,76793-57-2,77398-05-1,98103-08-3)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1016/S0008-6215(00)84673-X

Reference yield: 17.0%

(2S,3S,4S)-4-allyloxycarbonylamino-2-methyl-3-(4-nitrobenzoyloxy)-3,4-dihydro-2H-pyran + trifluoroacetic acid (76-05-1) → (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran (77398-05-1)

Guidance literature:

(2S,3S,4S)-4-allyloxycarbonylamino-2-methyl-3-(4-nitrobenzoyloxy)-3,4-dihydro-2H-pyran; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

trifluoroacetic acid; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 48h; Inert atmosphere;

Reference yield:

methyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enopyranoside (33647-98-2) → 1,5-anhydro-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-xylo-hex-1-enitol (72384-25-9,73891-04-0,73891-07-3,76793-53-8,76793-57-2,77398-05-1,98103-08-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.17 h / 20 °C

2: 91 percent / sodium methoxide / methanol / 1 h / 20 °C

3: 95 percent / pyridine / 3 h / 0 °C

4: 1.) sodium azide; 2.) lithium aluminium hydride / 1.) bortrifluorid etherate / 1.) acetonitrile; 2.) ether, 20 min, 0 degC

5: 64 percent / triethylamine / CH₂Cl₂ / 0.33 h / 20 °C

6: 95 percent / pyridine / 16 h / 20 °C

With pyridine; lithium aluminium tetrahydride; sodium azide; sodium methylate; triethylamine; triphenylphosphine; diethylazodicarboxylate; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)84673-X

upstream raw materials:

4-nitro-benzoyl chloride

2,3,6-Trideoxy-3-trifluoroacetamido-L-lixo-hexopyranose

1,5-anhydro-2,3,6-tridesoxy-3-trifluoroacetamido-D-xylo-hex-1-enitol

3-amino-1,5-anhydro-2,3,6-tridesoxy-D-arabino-hex-1-enitol

Downstream raw materials:

7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-ribo-hexopyranosyl)daunomycinone

7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-D-arabino-hexopyranosyl)daunomycinone

7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranosyl)daunomycinone

4-Nitro-benzoic acid (2R,3R,4S,6S)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester