(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

Base Information

• Chemical Name: (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
• CAS No.: 156624-85-0
• Molecular Formula: C₅₂H₈₃NO₁₀Si
• Molecular Weight: 910.317

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 1 articles about (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 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: 41.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (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,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)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; 1.) -70 deg C, 1.25 h, 2.) 0 deg C, 2 h;

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

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:

(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) → 28-phenyl-FK506

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 23 percent / 48percent HF / acetonitrile / 3 h

With pyridine; hydrogen fluoride; Dess-Martin periodane; In dichloromethane; acetonitrile;

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

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(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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