(2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol

Base Information

• Chemical Name: (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol
• CAS No.: 242808-77-1
• Molecular Formula: C₂₄H₃₆O₆
• Molecular Weight: 420.546

Synonyms:(2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol

Chemical Property of (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol

Chemical Property:

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Technology Process of (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol

There total 24 articles about (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol 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: 44.0%

(2R,3S)-2-[4-((2S,3R)-3-Benzyloxy-oxepan-2-yl)-3-ethanesulfinyl-3-ethylsulfanyl-2-hydroxy-butyl]-oxepan-3-ol (245053-92-3) + trimethyl orthoformate (149-73-5) → (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol (242808-77-1) + (2R,3S,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol (242808-79-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 - 25 ℃;

DOI:10.1055/s-1999-2784

Reference yield:

[3-(2-Benzyloxy-ethyl)-oxiranyl]-methanol (85531-70-0) → (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol (242808-77-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / Ti(i-PrO)4 / toluene / 5 h / Heating

2: DMAP, pyridine / CH₂Cl₂ / 14 h / 20 - 25 °C

3: K₂CO₃ / methanol / 6 h / 20 - 23 °C

4: 1.) CuCN / 1.) THF, -78 to -40 deg C, 1 h, 2.) THF, -40 deg C, 1.3 h

5: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

6: H₂ / RhCl(PPh₃)3 / benzene / 9 h / 21 °C

7: imidazole / dimethylformamide / 3 h / 24 °C

8: H₂ / 10 percent Pd/C / methanol / 2 h / 21 °C

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

10: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

11: TBAF / tetrahydrofuran / 25 °C

12: 44 percent / TsOH*H₂O / methanol / 20 - 25 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; RhCl(PPh₃)3; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1055/s-1999-2784

Reference yield:

(S)-2-((R)-1-Allyloxy-3-benzyloxy-propyl)-oxirane (242808-61-3) → (2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-2-methoxy-octahydro-1,5-dioxa-benzocyclohepten-3-ol (242808-77-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) CuCN / 1.) THF, -78 to -40 deg C, 1 h, 2.) THF, -40 deg C, 1.3 h

2: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

3: H₂ / RhCl(PPh₃)3 / benzene / 9 h / 21 °C

4: imidazole / dimethylformamide / 3 h / 24 °C

5: H₂ / 10 percent Pd/C / methanol / 2 h / 21 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

7: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

8: TBAF / tetrahydrofuran / 25 °C

9: 44 percent / TsOH*H₂O / methanol / 20 - 25 °C

With 1H-imidazole; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; RhCl(PPh₃)3; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1999-2784

upstream raw materials:

(2R,3S)-2-[4-((2S,3R)-3-Benzyloxy-oxepan-2-yl)-3-ethanesulfinyl-3-ethylsulfanyl-2-hydroxy-butyl]-oxepan-3-ol

trimethyl orthoformate

[3-(2-Benzyloxy-ethyl)-oxiranyl]-methanol

(S)-2-((R)-1-Allyloxy-3-benzyloxy-propyl)-oxirane

Downstream raw materials:

(2R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-hexahydro-1,5-dioxa-benzocyclohepten-3-one

(2R,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-3-ol

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