Erythromycin B

Base Information

• Chemical Name: Erythromycin B
• CAS No.: 527-75-3
• Deprecated CAS: 34140-61-9
• Molecular Formula: C₃₇H₆₇NO₁₂
• Molecular Weight: 717.938
• Hs Code.: 2941500000
• European Community (EC) Number: 809-313-4
• UNII: AN686JJ1YI
• DSSTox Substance ID: DTXSID501023765
• Nikkaji Number: J69H
• Wikidata: Q27103559
• NCI Thesaurus Code: C171821
• Metabolomics Workbench ID: 21284
• ChEMBL ID: CHEMBL3220708
• Mol file: 527-75-3.mol

Synonyms:12-deoxyerythromycin A;berythromycin;berythromycin, (8S)-isomer;erythromycin B

Chemical Property of Erythromycin B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 168-170oC (dec)
• Boiling Point: 807.578°C at 760 mmHg
• PKA: 13.49±0.70(Predicted)
• Flash Point: 442.207°C
• PSA: 173.68000
• Density: 1.176g/cm³
• LogP: 2.67070
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 717.46632657
• Heavy Atom Count: 50
• Complexity: 1130

Purity/Quality:

98%Min ^*data from raw suppliers

ErythromycinB(~90%) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)C
• Isomeric SMILES: CC[C@@H]1[C@@H]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)C
• Uses: Erythromycin B (12-deoxyerythromycin A) is a minor co-metabolite of erythromycin produced Saccharopolyspora erythreae. Erythromycin B exhibits broad spectrum antibiotic activity, albeit less potent than erythromycin A. Erythromycin B played an integral part of the SAR studies of semi-synthetic erythromycins, however none reached clinical development. Erythromycin B is a co-metabolite of Erythromycin A (E649950), an antibacterial agent.

Technology Process of Erythromycin B

There total 40 articles about Erythromycin B 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%

(9S)-3-O-(α-L-cladinosyl)-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide B (944740-86-7) → erythromycin B (527-75-3)

Guidance literature:

With methanol; for 8h; Heating;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one (188785-99-1) → erythromycin B (527-75-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

1.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

3.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

4.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C

5.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH₂Cl₂ / 2 h / 20 °C

6.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 5 h / -78 °C

7.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

8.1: ozone; pyridine; Sudan III / CH₂Cl₂ / -78 °C

8.2: 85 percent / triphenylphosphine / CH₂Cl₂ / 2 h / 20 °C

9.1: 100 percent / Na₂HPO₄; m-CPBA / tetrahydrofuran; H₂O / 15 h / 20 °C

10.1: 99 percent / hydrogen / palladium on charcoal / methanol; tetrahydrofuran / 3.5 h / 20 °C

11.1: 93 percent / 4-dimethylaminopyridine; triethylamine; 2,3,4-trichlorobenzoyl chloride / toluene / 0.25 h / 20 °C

12.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 28 h / 60 °C

13.1: 70 percent / KH₂PO₄; aq. HCl / tetrahydrofuran / 14 h / 50 °C

14.1: 61 percent / silver triflate; molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 1 h / 0 °C

15.1: 40 percent / copper(II) oxide; molecular sieves 4 Angstroem; copper(II) trifluoromethanesulfonate / acetonitrile / 2 h / 20 °C

16.1: acetic acid; water / 14 h / 35 °C

17.1: 8.7 mg / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

18.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 14 h / 20 °C

19.1: 95 percent / aq. MeOH / 8 h / Heating

With pyridine; hydrogenchloride; methanol; dmap; disodium hydrogenphosphate; potassium dihydrogenphosphate; oil scarlet; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silver trifluoromethanesulfonate; tetramethylammonium borohydride; copper(II) bis(trifluoromethanesulfonate); Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 5.1: Dess-Martin oxidation / 11.1: Yamaguchi lactonization / 18.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (188785-95-7) → erythromycin B (527-75-3)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 85 percent / CaCO₃; Hg(ClO₄)2 / tetrahydrofuran; H₂O / 0.25 h / 20 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

2.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

4.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

5.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C

6.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH₂Cl₂ / 2 h / 20 °C

7.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 5 h / -78 °C

8.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

9.1: ozone; pyridine; Sudan III / CH₂Cl₂ / -78 °C

9.2: 85 percent / triphenylphosphine / CH₂Cl₂ / 2 h / 20 °C

10.1: 100 percent / Na₂HPO₄; m-CPBA / tetrahydrofuran; H₂O / 15 h / 20 °C

11.1: 99 percent / hydrogen / palladium on charcoal / methanol; tetrahydrofuran / 3.5 h / 20 °C

12.1: 93 percent / 4-dimethylaminopyridine; triethylamine; 2,3,4-trichlorobenzoyl chloride / toluene / 0.25 h / 20 °C

13.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 28 h / 60 °C

14.1: 70 percent / KH₂PO₄; aq. HCl / tetrahydrofuran / 14 h / 50 °C

15.1: 61 percent / silver triflate; molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 1 h / 0 °C

16.1: 40 percent / copper(II) oxide; molecular sieves 4 Angstroem; copper(II) trifluoromethanesulfonate / acetonitrile / 2 h / 20 °C

17.1: acetic acid; water / 14 h / 35 °C

18.1: 8.7 mg / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

19.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 14 h / 20 °C

20.1: 95 percent / aq. MeOH / 8 h / Heating

With pyridine; hydrogenchloride; methanol; dmap; disodium hydrogenphosphate; potassium dihydrogenphosphate; mercury(II) perchlorate; oil scarlet; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silver trifluoromethanesulfonate; tetramethylammonium borohydride; copper(II) bis(trifluoromethanesulfonate); Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; copper(II) oxide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 6.1: Dess-Martin oxidation / 12.1: Yamaguchi lactonization / 19.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

9,9-dihydro-erythromycin B

(9S)-3-O-(α-L-cladinosyl)-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide B

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecane-7,9-diol

Downstream raw materials:

C₅₉H₁₀₇NO₁₃Si₂

C₄₇H₇₇NO₁₄

C₄₇H₇₅NO₁₃

Refernces

• 1、 Martin,Hida,Kym,Loft,Hodgson. "The asymmetric synthesis of erythromycin B". . p. 3193 - 3194. Retrieved 2007/10/03.
• 2、 Kurath,Jones,Egan,Perun. "Acid degradation of erythromycin A and erythromycin B.". . p. 362 - 362. Retrieved 2007/10/07.