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

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-13,14-diethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 484670-89-5
• Molecular Formula: C₃₈H₅₇NO₁₀
• Molecular Weight: 687.871
• Mol file: 484670-89-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-13,14-diethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-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: 94.0%

Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,4S,5S,6R,7R,9R,13S,14R)-13,14-diethyl-4,13-dihydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,10-dioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester (484670-88-4) → Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-13,14-diethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester (484670-89-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 2h;

DOI:10.1016/j.bmc.2006.04.032

Reference yield:

C55H81NO15 → Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-13,14-diethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester (484670-89-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CuBr*Me₂S / diethyl ether / -78 - -20 °C

1.2: diethyl ether / 12 h / 0 - 5 °C

1.3: 3.52 g / pyridinium para-toluenesulfonate / acetonitrile; H₂O / 48 h / 70 °C

2.1: 67 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / -10 - -5 °C

3.1: 69 percent / pyridine / 18 h / 0 - 20 °C

4.1: 98 percent / DBU / acetone / 45 h / 20 - 60 °C

5.1: 82 percent / HCl / acetonitrile; H₂O / 22 h

6.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With pyridine; hydrogenchloride; copper(I) bromide dimethylsulfide complex; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/j.bmc.2006.04.032

Reference yield:

C53H79NO15 (484670-78-2) → Benzoic acid (2S,3R,4S,6R)-2-((E)-(3R,5R,6R,7R,9R,13S,14R)-13,14-diethyl-13-hydroxy-7-methoxy-3,5,7,9,11-pentamethyl-2,4,10-trioxo-oxacyclotetradec-11-en-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester (484670-89-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / pyridine / 18 h / 0 - 20 °C

2: 98 percent / DBU / acetone / 45 h / 20 - 60 °C

3: 82 percent / HCl / acetonitrile; H₂O / 22 h

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With pyridine; hydrogenchloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/j.bmc.2006.04.032

upstream raw materials:

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

C₅₃H₇₇NO₁₄

C₅₃H₈₁NO₁₅

C₅₃H₇₉NO₁₅

Downstream raw materials:

Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2,3-diethyl-9-methoxy-5,7,9,11,13-pentamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester