(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one

Base Information

• Chemical Name: (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one
• CAS No.: 193214-03-8
• Molecular Formula: C₁₉H₁₆N₂O₆
• Molecular Weight: 368.346

Synonyms:(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one

Chemical Property of (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one

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Technology Process of (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one

There total 1 articles about (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one 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: 21.0%

4-nitrobenzaldehdye (555-16-8) + (S)-4-(2-Diazo-acetyl)-5-phenyl-morpholin-3-one → (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.01,6]undecan-7-one (193214-03-8)

Guidance literature:

dirhodium tetraacetate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)00919-2

Reference yield: 94.0%

(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.01,6]undecan-7-one (193214-03-8) → (S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one (193214-06-1)

Guidance literature:

With water; hydrogen cation; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)00919-2

Reference yield:

(1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.01,6]undecan-7-one (193214-03-8) → (2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (142917-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / H(+), H₂O / tetrahydrofuran

2: 74 percent / LiOH/H₂O₂ / tetrahydrofuran; H₂O

3: 71 percent / TMSCl

With lithium hydroxide; chloro-trimethyl-silane; water; dihydrogen peroxide; hydrogen cation; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(97)00919-2

upstream raw materials:

4-nitrobenzaldehdye

Downstream raw materials:

(S)-4-[(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionyl]-5-phenyl-morpholin-3-one

(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester

(2S,3R)-3-(4-cyanophenyl)-2,3-dihydroxypropanoic acid

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