Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:484671-60-5
Molecular Formula:C₃₈H₅₅NO₁₀
Molecular Weight:685.855
Hs Code.:

Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Synonyms:Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 14 articles about Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl 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: 51.0%

: 484671-59-2
Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-formyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

: 1779-49-3
Methyltriphenylphosphonium bromide

: 484671-60-5
Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-formyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 5h;
DOI:10.1021/jm051157a

Reference yield:

: 484670-62-4
C₅₅H₈₁NO₁₄

: 484671-60-5
Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / pyridinium p-toluenesulfonate / acetonitrile; H₂O / 17 h / 68 °C

2.1: 82 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 4 h / 20 °C

3.1: diisopropylethylamine; (dimethylamino)pyridine / CH₂Cl₂ / 17 h / -10 °C

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 14 h / 0 °C

5.1: 100 percent / pyridine / 18 h / 0 °C

6.1: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 45 h / 20 - 68 °C

7.1: 46.0 g / aq. HCl / 12 h / 40 °C

8.1: 99 percent / methyl sulfide; diisopropylethylamine; N-chlorosuccinimide / tetrahydrofuran / -15 - -10 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

9.2: 51 percent / tetrahydrofuran; toluene / 5 h / -78 - 20 °C

With pyridine; hydrogenchloride; dmap; N-chloro-succinimide; osmium(VIII) oxide; dimethylsulfide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; 4.1: Dess-Martin oxidation;
DOI:10.1021/jm051157a

Reference yield:

: 484671-58-1
Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,4S,5S,6R,7R,9R,13R,14R)-14-ethyl-4,13-dihydroxy-13-hydroxymethyl-7-methoxy-3,5,7,9,11-pentamethyl-2,10-dioxo-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

: 484671-60-5
Benzoic acid (2S,3R,4S,6R)-4-dimethylamino-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-13-vinyl-oxacyclotetradec-11-en-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / methyl sulfide; diisopropylethylamine; N-chlorosuccinimide / tetrahydrofuran / -15 - -10 °C

2.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 51 percent / tetrahydrofuran; toluene / 5 h / -78 - 20 °C

With N-chloro-succinimide; dimethylsulfide; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; toluene;
DOI:10.1021/jm051157a