(2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine

Base Information

• Chemical Name: (2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine
• CAS No.: 1258505-37-1
• Molecular Formula: C₂₄H₃₁NO₉S
• Molecular Weight: 509.577

Synonyms:(2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine

Chemical Property of (2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine

There total 1 articles about (2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine 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: 63.0%

3,4-di-O-acetyl-1,4-anhydro-N-(2,2-diethoxycarbonylvinyl)-α-L-arabinopyranosylamine (1258505-13-3) + para-thiocresol (106-45-6) → (2R,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine (1258505-42-8) + (2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine (1258505-37-1)

Guidance literature:

3,4-di-O-acetyl-1,4-anhydro-N-(2,2-diethoxycarbonylvinyl)-α-L-arabinopyranosylamine; With boron trifluoride diethyl etherate; In diethyl ether; at 20 ℃; Molecular sieve; Inert atmosphere;

para-thiocresol; In diethyl ether; at 20 ℃; for 1h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2010.09.065

Reference yield: 85.0%

(2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine (1258505-37-1) → (2S,3R,4S,5S)-3,4-dihydroxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine (1258505-43-9)

Guidance literature:

With methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2010.09.065

Reference yield: 80.0%

(2S,3R,4S,5S)-3,4-di-acetoxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine (1258505-37-1) → (7S,8R,9R,10S) 1-aza-3-ethoxycarbonyl-8,9-dihydroxy-5-oxa-4-oxo-10-(p-tolylthio)bicyclo[5,3,0]dec-2-ene (1258505-46-2)

Guidance literature:

With methanol; at 40 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.tet.2010.09.065

upstream raw materials:

3,4-di-O-acetyl-1,4-anhydro-N-(2,2-diethoxycarbonylvinyl)-α-L-arabinopyranosylamine

para-thiocresol

Downstream raw materials:

(2S,3R,4S,5S)-3,4-dihydroxy-N-(2,2-diethoxycarbonylvinyl)-5-hydroxymethyl-2-p-tolylthiopyrrolidine

(7S,8R,9R,10S) 1-aza-3-ethoxycarbonyl-8,9-dihydroxy-5-oxa-4-oxo-10-(p-tolylthio)bicyclo[5,3,0]dec-2-ene

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