(2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate
• CAS No.: 1443534-18-6
• Molecular Formula: C₂₄H₂₂ClNO₈S
• Molecular Weight: 521.949

Synonyms:(2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

Chemical Property of (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

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Technology Process of (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

There total 5 articles about (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 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: 56.0%

(2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate + 2-(2-(4-chlorophenyl)[2-14C]-1,3-thiazol-4-yl)acetic acid + fenclozic acid (17969-20-9) → (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-14C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1443534-18-6)

Guidance literature:

(2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate; 2-(2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl)acetic acid; fenclozic acid; With 4-methyl-morpholine; HATU; In acetonitrile; at 20 - 22 ℃; for 24h; Inert atmosphere;

In acetonitrile; Acidic conditions; Inert atmosphere;

DOI:10.1002/jlcr.2985

Reference yield:

1-Chloro-4-iodobenzene (637-87-6) → (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-14C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1443534-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene / acetone / 4.5 h / 40 °C / Inert atmosphere

2.1: diammonium sulfide / methanol / 0.5 h / 80 °C / Sealed tube; Microwave irradiation

3.1: methanol / 0.5 h / 100 °C / Sealed tube; Microwave irradiation

4.1: sodium hydroxide / methanol / 0.25 h / 50 °C / Sealed tube; Microwave irradiation

4.2: pH 5 - 6 / Sealed tube; Microwave irradiation

5.1: HATU; 4-methyl-morpholine / acetonitrile / 24 h / 20 - 22 °C / Inert atmosphere

5.2: Amberlyst A-15 / Acidic conditions; Inert atmosphere

With 4-methyl-morpholine; 1,1'-bis-(diphenylphosphino)ferrocene; diammonium sulfide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; HATU; sodium hydroxide; In methanol; acetone; acetonitrile;

DOI:10.1002/jlcr.2985

Reference yield:

4-chlorobenzo[14C]nitrile → (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-14C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1443534-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diammonium sulfide / methanol / 0.5 h / 80 °C / Sealed tube; Microwave irradiation

2.1: methanol / 0.5 h / 100 °C / Sealed tube; Microwave irradiation

3.1: sodium hydroxide / methanol / 0.25 h / 50 °C / Sealed tube; Microwave irradiation

3.2: pH 5 - 6 / Sealed tube; Microwave irradiation

4.1: HATU; 4-methyl-morpholine / acetonitrile / 24 h / 20 - 22 °C / Inert atmosphere

4.2: Amberlyst A-15 / Acidic conditions; Inert atmosphere

With 4-methyl-morpholine; diammonium sulfide; HATU; sodium hydroxide; In methanol; acetonitrile;

DOI:10.1002/jlcr.2985

upstream raw materials:

fenclozic acid

1-Chloro-4-iodobenzene

4-chlorobenzothio[¹⁴C]amide

Downstream raw materials:

(2S,3S,4S,5R,6S)-6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

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