(3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene

Base Information

• Chemical Name: (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene
• CAS No.: 1263469-89-1
• Molecular Formula: C₃₅H₅₂O₂
• Molecular Weight: 504.797

Synonyms:

Chemical Property of (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene

There total 15 articles about (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 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:

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)benzo[d]thiazole (1263469-81-3) + (R)-2-(benzyloxy)-3-methylbutanal (96925-01-8,110840-39-6,149342-56-3,84994-60-5) → (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-89-1) + (3α,5R,6β,22E,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-88-0)

Guidance literature:

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)benzo[d]thiazole; With sodium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 0.25h; Inert atmosphere;

(R)-2-(benzyloxy)-3-methylbutanal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃; for 6h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol102936z

Reference yield:

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)benzo[d]thiazole (1263469-81-3) + (d,l) isopropylidene glyceraldehyde (5736-03-8) → (3α,5R,6β,22Z,24S)-6-methoxy-3,5-cyclo-26,27-dinorcholest-22-ene-24,25-diol cyclic 1-methylethylidene acetal + (3α,5R,6β,22E,24S)-6-methoxy-3,5-cyclo-26,27-dinorcholest-22-ene-24,25-diol cyclic 1-methylethylidene acetal + (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-89-1) + (3α,5R,6β,22E,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-88-0)

Guidance literature:

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)benzo[d]thiazole; With sodium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 0.25h; Inert atmosphere;

(d,l) isopropylidene glyceraldehyde; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃; for 6h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol102936z

Reference yield:

3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether (51231-23-3) → (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-89-1) + (3α,5R,6β,22E,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene (1263469-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 0 °C

2.1: ammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tetrahydrofuran; ethanol / 2 h / 70 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.25 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 - 20 °C / Inert atmosphere

With ammonium heptamolybdate tetrahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; sodium hexamethyldisilazane; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; 1.1: Mitsunobu reaction / 3.1: Julia Olefin synthesis / 3.2: Julia Olefin synthesis;

DOI:10.1021/ol102936z

upstream raw materials:

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)thio)benzo[d]thiazole

2-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)benzo[d]thiazole

(R)-2-(benzyloxy)-3-methylbutanal

(d,l) isopropylidene glyceraldehyde

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