(E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

Base Information

• Chemical Name: (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone
• CAS No.: 156624-86-1
• Molecular Formula: C₅₂H₈₁NO₁₀Si
• Molecular Weight: 908.301

Synonyms:(E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

Chemical Property of (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

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Technology Process of (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

There total 3 articles about (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone 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: 84.0%

(E)-(1R,9S,12S,13S,14S,16R,17R,21S,23S,24R,25S,27R)-17-Allyl-1,16-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10-trione (156624-85-0) → (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (156624-86-1)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80796-1

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (156624-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -70 deg C, 1.25 h, 2.) 0 deg C, 2 h

2: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; Dess-Martin periodane; In dichloromethane;

DOI:10.1016/S0040-4020(01)80796-1

Reference yield:

(E)-(1R,9S,12S,13R,14S,16R,17R,21S,23S,24R,25S,27R)-17-Allyl-1,14,16-trihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10-trione → (E)-(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (156624-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -70 deg C, 1.25 h, 2.) 0 deg C, 2 h

2: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; Dess-Martin periodane; In dichloromethane;

DOI:10.1016/S0040-4020(01)80796-1

upstream raw materials:

(E)-(1R,9S,12S,13S,14S,16R,17R,21S,23S,24R,25S,27R)-17-Allyl-1,16-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-12-((E)-1-methyl-2-phenyl-vinyl)-14-triisopropylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10-trione

triisopropylsilyl trifluoromethanesulfonate

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