[(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane
• CAS No.: 129368-33-8
• Molecular Formula: C₄₉H₆₂O₆SSi
• Molecular Weight: 807.179

Synonyms:

Chemical Property of [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane

There total 18 articles about [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane 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:

(3aS,5S,6aS)-2-Ethoxy-hexahydro-cyclopenta[b]furan-5-ol (129393-13-1) → [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane (129368-33-8)

Guidance literature:

Multi-step reaction with 17 steps

1: NaH / tetrahydrofuran; dimethylformamide / Ambient temperature

2: 1N HCl / 1,2-dimethoxy-ethane / Ambient temperature

3: Jones reagent / acetone / 0 °C

4: 1) LDA / 2) THF, HMPA, -78 deg C

5: Et₃N / CH₂Cl₂ / -10 °C

6: DBU / benzene / 50 °C

7: 1) Et₂O, CH₂Cl₂, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH₃

8: 83 percent / LiAlH₄ / diethyl ether / -10 °C

9: imidazole / dimethylformamide / Ambient temperature

10: i-Pr₂NEt / 1,2-dichloro-ethane / 50 °C

11: aq. AcOH / tetrahydrofuran / 60 °C

12: Swern oxidation

13: t-BuOK / tetrahydrofuran / -78 deg C -> room temperature

14: DIBAL / hexane; CH₂Cl₂ / -78 °C

15: n-Bu₃P / benzene / Ambient temperature

16: 2KHSO₅*KHSO₄*K₂SO₄ / tetrahydrofuran; methanol; H₂O / Ambient temperature

17: 1) n-BuLi / 1) THF, HMPA, -78 deg C

With 1H-imidazole; hydrogenchloride; potassium sulfate; potassium hydrogensulfate; lithium aluminium tetrahydride; potassium peroxomonosulfate; n-butyllithium; jones reagent; tributylphosphine; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0040-4039(90)80020-M

Reference yield:

(3aR,6aS)-2-Ethoxy-hexahydro-cyclopenta[b]furan-5-one (126958-23-4,127061-40-9,129444-45-7) → [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane (129368-33-8)

Guidance literature:

Multi-step reaction with 18 steps

1: NaBH₄ / methanol / 0 °C

2: NaH / tetrahydrofuran; dimethylformamide / Ambient temperature

3: 1N HCl / 1,2-dimethoxy-ethane / Ambient temperature

4: Jones reagent / acetone / 0 °C

5: 1) LDA / 2) THF, HMPA, -78 deg C

6: Et₃N / CH₂Cl₂ / -10 °C

7: DBU / benzene / 50 °C

8: 1) Et₂O, CH₂Cl₂, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH₃

9: 83 percent / LiAlH₄ / diethyl ether / -10 °C

10: imidazole / dimethylformamide / Ambient temperature

11: i-Pr₂NEt / 1,2-dichloro-ethane / 50 °C

12: aq. AcOH / tetrahydrofuran / 60 °C

13: Swern oxidation

14: t-BuOK / tetrahydrofuran / -78 deg C -> room temperature

15: DIBAL / hexane; CH₂Cl₂ / -78 °C

16: n-Bu₃P / benzene / Ambient temperature

17: 2KHSO₅*KHSO₄*K₂SO₄ / tetrahydrofuran; methanol; H₂O / Ambient temperature

18: 1) n-BuLi / 1) THF, HMPA, -78 deg C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; potassium sulfate; potassium hydrogensulfate; lithium aluminium tetrahydride; potassium peroxomonosulfate; n-butyllithium; jones reagent; tributylphosphine; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0040-4039(90)80020-M

Reference yield:

(3aS,5S,6aS)-5-Benzyloxy-hexahydro-cyclopenta[b]furan-2-ol (114544-33-1) → [(1R,2S)-2-((E)-3-Benzenesulfonyl-2,6-dimethyl-hepta-1,5-dienyl)-1-((1S,2S,4S)-4-benzyloxy-2-methoxymethoxy-cyclopentyl)-cyclopropylmethoxy]-tert-butyl-diphenyl-silane (129368-33-8)

Guidance literature:

Multi-step reaction with 15 steps

1: Jones reagent / acetone / 0 °C

2: 1) LDA / 2) THF, HMPA, -78 deg C

3: Et₃N / CH₂Cl₂ / -10 °C

4: DBU / benzene / 50 °C

5: 1) Et₂O, CH₂Cl₂, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH₃

6: 83 percent / LiAlH₄ / diethyl ether / -10 °C

7: imidazole / dimethylformamide / Ambient temperature

8: i-Pr₂NEt / 1,2-dichloro-ethane / 50 °C

9: aq. AcOH / tetrahydrofuran / 60 °C

10: Swern oxidation

11: t-BuOK / tetrahydrofuran / -78 deg C -> room temperature

12: DIBAL / hexane; CH₂Cl₂ / -78 °C

13: n-Bu₃P / benzene / Ambient temperature

14: 2KHSO₅*KHSO₄*K₂SO₄ / tetrahydrofuran; methanol; H₂O / Ambient temperature

15: 1) n-BuLi / 1) THF, HMPA, -78 deg C

With 1H-imidazole; potassium sulfate; potassium hydrogensulfate; lithium aluminium tetrahydride; potassium peroxomonosulfate; n-butyllithium; jones reagent; tributylphosphine; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0040-4039(90)80020-M

upstream raw materials:

(3aS,5S,6aS)-2-Ethoxy-hexahydro-cyclopenta[b]furan-5-ol

(3aR,6aS)-2-Ethoxy-hexahydro-cyclopenta[b]furan-5-one

(3aS,5S,6aS)-5-Benzyloxy-hexahydro-cyclopenta[b]furan-2-ol

(3aS,5S,6aS)-5-Benzyloxy-hexahydro-cyclopenta[b]furan-2-one

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