(S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester
• CAS No.: 860812-22-2
• Molecular Formula: C₂₅H₃₁NO₁₁
• Molecular Weight: 521.521

Synonyms:(S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester

Chemical Property of (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester

Chemical Property:

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Technology Process of (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester

There total 2 articles about (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl 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: 91.0%

(1R,3R,4S,5R)-1,3,4,5-tetraacetoxycyclohexane-1-carboxylic acid chloride (92651-21-3,92822-51-0,95463-24-4) → (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester (860812-22-2)

Guidance literature:

With Amberlyst A-21; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1016/j.bmcl.2005.05.004

Reference yield:

(1R,3R,4R,5R)-(-)-quinic acid tetraacetate (32469-24-2) → (S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester (860812-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂; Amberlyst A-21 / CH₂Cl₂ / 4 h / 20 °C

2: 91 percent / Amberlyst A-21 / CH₂Cl₂ / 14 h / 20 °C

With thionyl chloride; Amberlyst A-21; In dichloromethane;

DOI:10.1016/j.bmcl.2005.05.004

Reference yield:

(S)-2-[((3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarbonyl)-amino]-propionic acid benzyl ester (860812-22-2) → (S)-2-[((3R,5R)-1,3,4,5-Tetrahydroxy-cyclohexanecarbonyl)-amino]-propionic acid

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1016/j.bmcl.2005.05.004

upstream raw materials:

(1R,3R,4S,5R)-1,3,4,5-tetraacetoxycyclohexane-1-carboxylic acid chloride

(1R,3R,4R,5R)-(-)-quinic acid tetraacetate

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