2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester

Base Information

• Chemical Name: 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester
• CAS No.: 709669-24-9
• Molecular Formula: C₄₀H₄₅FNO₁₁PS
• Molecular Weight: 797.836

Synonyms:2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester

Chemical Property of 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester

There total 10 articles about 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl 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:

N-acetyl-D-galactosamine (72-87-7,1136-42-1,1136-44-3,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4,6082-29-7) → 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester (709669-24-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / BF₃*Et₂O / 2 h / 70 °C

2: 75 percent / (+/-)-camphorsulfonic acid / dimethylformamide / 12 h / 20 °C

3: 66 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 40 °C

4: 81 percent / NaBH₃CN; molecular sieves 4 Angstroem; HCl / tetrahydrofuran; diethyl ether / 1 h / 0 °C

5: 60 percent / (diethylamino)sulfur trifluoride; pyridine / CH₂Cl₂ / -20 - 20 °C

6: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 20 °C

7: 87 percent / sodium hydride / tetrahydrofuran / 18 h / 40 °C

8: 72 percent / 4-(dimethylamino)pyridine; CH₃CH₃N=C=N(CH₂)3N(CH₃)2*HCl / CH₂Cl₂ / 6 h / 20 °C

9: 90 percent / (1,5-cyclooctadiene)(MePPh₂)2iridium(I) hexafluorophosphate; H₂; I₂ / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

10: 1,2,4-triazole / CH₂Cl₂ / 0.75 h / Heating

With pyridine; 1,2,4-Triazole; hydrogenchloride; dmap; 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; diethylamino-sulfur trifluoride; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol049598w

Reference yield:

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide (64650-83-5) → 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester (709669-24-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 75 percent / (+/-)-camphorsulfonic acid / dimethylformamide / 12 h / 20 °C

2: 66 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 40 °C

3: 81 percent / NaBH₃CN; molecular sieves 4 Angstroem; HCl / tetrahydrofuran; diethyl ether / 1 h / 0 °C

4: 60 percent / (diethylamino)sulfur trifluoride; pyridine / CH₂Cl₂ / -20 - 20 °C

5: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 20 °C

6: 87 percent / sodium hydride / tetrahydrofuran / 18 h / 40 °C

7: 72 percent / 4-(dimethylamino)pyridine; CH₃CH₃N=C=N(CH₂)3N(CH₃)2*HCl / CH₂Cl₂ / 6 h / 20 °C

8: 90 percent / (1,5-cyclooctadiene)(MePPh₂)2iridium(I) hexafluorophosphate; H₂; I₂ / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

9: 1,2,4-triazole / CH₂Cl₂ / 0.75 h / Heating

With pyridine; 1,2,4-Triazole; hydrogenchloride; dmap; 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; diethylamino-sulfur trifluoride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol049598w

Reference yield:

allyl 2-acetamido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside (92841-84-4) → 2-N-acetyl-6-O-benzyl-1-α(β)-O-di(benzyloxy)phosphanyl-4-deoxy-4-fluoro-muramic acid 2-(phenylsulfonyl)ethyl ester (709669-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 40 °C

2: 81 percent / NaBH₃CN; molecular sieves 4 Angstroem; HCl / tetrahydrofuran; diethyl ether / 1 h / 0 °C

3: 60 percent / (diethylamino)sulfur trifluoride; pyridine / CH₂Cl₂ / -20 - 20 °C

4: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 20 °C

5: 87 percent / sodium hydride / tetrahydrofuran / 18 h / 40 °C

6: 72 percent / 4-(dimethylamino)pyridine; CH₃CH₃N=C=N(CH₂)3N(CH₃)2*HCl / CH₂Cl₂ / 6 h / 20 °C

7: 90 percent / (1,5-cyclooctadiene)(MePPh₂)2iridium(I) hexafluorophosphate; H₂; I₂ / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

8: 1,2,4-triazole / CH₂Cl₂ / 0.75 h / Heating

With pyridine; 1,2,4-Triazole; hydrogenchloride; dmap; 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; diethylamino-sulfur trifluoride; 4 A molecular sieve; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1021/ol049598w

upstream raw materials:

dibenzyl N,N-diethylphosphoramidite

N-acetyl-D-galactosamine

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

allyl 2-acetamido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside

Downstream raw materials:

C₅₆H₇₄F₄N₇O₁₈P

2-N-acetyl-6-O-benzyl-1-α-O-dibenzylphosphoryl-4-deoxy-4-fluoro-muramic acid

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