5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

Base Information

Chemical Name:5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A
CAS No.:300840-70-4
Molecular Formula:C₃₇H₅₅NO₁₀
Molecular Weight:673.844
Hs Code.:

Synonyms:5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

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Chemical Property of 5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

Chemical Property:

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Technology Process of 5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

There total 10 articles about 5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A 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: 79.0%

: 300840-69-1
2'-O-benzoyl-6-O-methyl-4''-O-methanesulfonyl-10,11-anhydro-14,15-dehydroerythromycin A

: 300840-70-4
5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

Guidance literature:: With hydrogenchloride; In acetonitrile; for 22h;
DOI:10.7164/antibiotics.54.278

Reference yield:

: 300840-55-5
6-O-methyl-14,15-dehydroerythromycin A

: 300840-70-4
5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

Guidance literature:: Multi-step reaction with 4 steps

1: 477 mg / Et₃N / CH₂Cl₂ / 48 h

2: 82 percent / pyridine / 24 h

3: 75 percent / DBU / acetone / 24 h

4: 79 percent / aq. HCl / acetonitrile / 22 h

With pyridine; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetone; acetonitrile;
DOI:10.7164/antibiotics.54.278

Reference yield:

: 14,15-dehydroerythromycin A

: 300840-70-4
5-O-(2'-O-benzoyl-desosaminyl)-10,11-anhydro-6-O-methyl-14,15-dehydroerythronolide A

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / hydroxylamine; AcOH / propan-2-ol; H₂O / 24 h / 50 °C

2: 83 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h

3: 97 percent / 1-trimethylsilylimidazole / CH₂Cl₂ / 0.17 h

4: KOt-Bu / tetrahydrofuran; dimethylsulfoxide; diethyl ether / 4 h / 0 °C

5: 245 mg / AcOH / acetonitrile; H₂O / 8 h

6: sodium hydrosulfite; formic acid / ethanol; H₂O / 2.5 h / 90 °C

7: 477 mg / Et₃N / CH₂Cl₂ / 48 h

8: 82 percent / pyridine / 24 h

9: 75 percent / DBU / acetone / 24 h

10: 79 percent / aq. HCl / acetonitrile / 22 h

With pyridine; hydrogenchloride; sodium disulfite; formic acid; potassium tert-butylate; hydroxylamine; pyridinium p-toluenesulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1-(Trimethylsilyl)imidazole; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; acetone; acetonitrile;
DOI:10.7164/antibiotics.54.278