Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester
• CAS No.: 190907-89-2
• Molecular Formula: C₃₇H₅₀N₂O₇SSi₂
• Molecular Weight: 723.05

Synonyms:Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester

Chemical Property of Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester

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Technology Process of Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester

There total 8 articles about Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl 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: 81.0%

p-Tolyl chlorothionoformate (937-63-3) + 2-(N-benzoylamino)-5-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]pyridine (190907-85-8) → Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester (190907-89-2)

Guidance literature:

With dmap; In acetonitrile; for 25h; Ambient temperature;

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester (190907-89-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / n-BuLi / tetrahydrofuran / 2.5 h / -75 °C

2: 1.) n-BuLi, 2.) Et₃SiH, BF₃*Et₂O / 1.) THF, -75 deg C, 3 h, -75 deg C -> 0 deg C, 4 h, 2.) CH₂Cl₂, -75 deg C -> rt, overnight

3: 1.) pyridine, 2.) BBr₃ / 1. )CH₂Cl₂, rt, 24 h, 2.) CH₂Cl₂, -75 deg C, 4 h

4: 75 percent / pyridine / 4 h / Ambient temperature

5: 81 percent / DMAP, 3A molecular sieves / acetonitrile / 25 h / Ambient temperature

With pyridine; triethylsilane; dmap; n-butyllithium; 3 A molecular sieve; boron trifluoride diethyl etherate; boron tribromide; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1021/ja9704904

Reference yield:

2-(N-benzoylamino)-5-(β-D-ribofuranosyl)pyridine (190907-82-5) → Thiocarbonic acid O-[(2S,3S,3aR,9aR)-2-(6-benzoylamino-pyridin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-p-tolyl ester (190907-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / pyridine / 4 h / Ambient temperature

2: 81 percent / DMAP, 3A molecular sieves / acetonitrile / 25 h / Ambient temperature

With dmap; 3 A molecular sieve; In pyridine; acetonitrile;

DOI:10.1021/ja9704904

upstream raw materials:

p-Tolyl chlorothionoformate

2-(N-benzoylamino)-5-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]pyridine

5-bromo-2-pyridylamine

benzoyl chloride

Downstream raw materials:

2-(N-benzoylamino)-5-(2'-deoxy-β-D-ribofuranosyl)pyridine

N-(5-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-pyridin-2-yl)-benzamide

2-(N-benzoylamino)-5-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-β-D-ribofuranosyl]pyridine

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