Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Base Information

• Chemical Name: Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester
• CAS No.: 114634-61-6
• Molecular Formula: C₃₇H₄₅NO₄SSe
• Molecular Weight: 678.795

Synonyms:Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Chemical Property of Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

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Technology Process of Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

There total 9 articles about Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-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: 97.0%

Acetic acid (E)-(1R,2R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (114651-83-1,114651-84-2) + C13H13Se2(1+)*BF4(1-) (114634-60-5) → Acetic acid (E)-(1R,2R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (114634-61-6,127354-85-2)

Guidance literature:

In dichloromethane; at -78 ℃; for 0.116667h;

DOI:10.1021/ja00167a037

Reference yield: 68.0%

C13H13Se2(1+)*BF4(1-) (114634-60-5) + Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (114651-83-1) → Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (114634-61-6)

Guidance literature:

DOI:10.1021/ja00222a047

Reference yield:

C32H43NO4SSi (114634-56-9) → Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (114634-61-6)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP, DBU / acetonitrile

2: LiN(SiMe₃)2 / tetrahydrofuran / -78 - -40 °C

3: HNEt₃F / tetrahydrofuran; methanol

4: DMAP, Et₃N / tetrahydrofuran

5: 1.) Me₃O(+)BF₄(-), Rieke zinc, DME 2.) K₂CO₃ / 1.) THF, HOAc, r.t.; 2.) MeOH

6: 68 percent

With dmap; 1,2-dimethoxyethane; trimethoxonium tetrafluoroborate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine hydrofluoride; triethylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja00222a047

upstream raw materials:

Acetic acid (E)-(1R,2R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

C₁₃H₁₃Se₂⁽¹⁺⁾*BF₄^(1-)

Acetic acid (E)-(1R,2R,3S,5R,7R,11R,14R,15S,16R)-17-acetyl-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Acetic acid (E)-(1R,3S,5R,7R,11R,14R,15S,16R)-16-benzyl-5,7,14-trimethyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Downstream raw materials:

Acetic acid (E)-(1R,3R,5S,7S,11R,12S,14S,15R,16S)-16-benzyl-12-hydroxy-5,7,14-trimethyl-13-methylene-3-methylsulfanyl-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadec-9-en-2-yl ester

d,l-zygosporin E

d,l-zygosporin E

Acetic acid (E)-(1S,2R,3S,5R,7R,11S,12R,14R,15S,16R)-16-benzyl-12-hydroxy-3-methanesulfinyl-5,7,14-trimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadec-9-en-2-yl ester

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