(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 845440-59-7
• Molecular Formula: C₅₄H₇₇NO₁₃SSi₂
• Molecular Weight: 1036.44

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 1 articles about (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl 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: 70.0%

methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate + (R)-10-{(S)-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-ol → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (845440-59-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃;

DOI:10.1021/ol047741f

Reference yield: 80.0%

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (845440-59-7) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-7-hydroxy-10-{(S)-hydroxy-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-methyl}-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; at 20 ℃;

DOI:10.1021/ol047741f

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((R)-10-{(S)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-triethylsilanyloxy-methyl}-7-triisopropylsilanyloxy-10H-9-thia-phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (845440-59-7) → C39H41NO13S

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TBAF; AcOH / 20 °C

2: Pb(OAc)4; NaHCO₃ / CH₂Cl₂ / 0.08 h / 20 °C

With lead(IV) acetate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; acetic acid; In dichloromethane;

DOI:10.1021/ol047741f

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