[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]

Base Information

• Chemical Name: [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]
• CAS No.: 910469-83-9
• Molecular Formula: C₄₅H₇₂N₆O₁₃SSi₂
• Molecular Weight: 993.336

Synonyms:[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]

Chemical Property of [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]

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Technology Process of [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]

There total 4 articles about [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[N^α(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide] 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: 40.0%

(2S,4R)-1-(((benzyloxy)carbonyl)-L-valyl)-4-hydroxypyrrolidine-2-carboxylic acid (194033-06-2) + NAP-TSAO-T (672307-67-4) → [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[Nα(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide] (910469-83-9)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jm0606490

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[Nα(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide] (910469-83-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / (benzotriazol-1-yl-oxy)-tris(dimethylamino)phosphonium*PF₆; TEA / CH₂Cl₂ / 15 h / 20 °C

2: 98 percent / aq. NaOH / methanol / 20 °C

3: 40 percent / (benzotriazol-1-yl-oxy)-tris(dimethylamino)phosphonium*PF₆; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With sodium hydroxide; TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jm0606490

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[Nα(benzyloxycarbonyl)-valyl-(2S,4R)-4-O-hydroxyprolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide] (910469-83-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / (benzotriazol-1-yl-oxy)-tris(dimethylamino)phosphonium*PF₆; TEA / CH₂Cl₂ / 15 h / 20 °C

2: 98 percent / aq. NaOH / methanol / 20 °C

3: 40 percent / (benzotriazol-1-yl-oxy)-tris(dimethylamino)phosphonium*PF₆; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With sodium hydroxide; TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jm0606490

upstream raw materials:

(2S,4R)-1-(((benzyloxy)carbonyl)-L-valyl)-4-hydroxypyrrolidine-2-carboxylic acid

NAP-TSAO-T

(S)-N-(benzyloxycarbonyl)valine

L-4-hydroxyproline methyl ester hydrochloride

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