{(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane
• CAS No.: 155853-18-2
• Molecular Formula: C₃₅H₆₀O₈Si
• Molecular Weight: 636.942
• Mol file: 155853-18-2.mol

Synonyms:

Chemical Property of {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane

There total 21 articles about {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-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: 26.0%

[(S)-2-[(1R,2R,4S)-2-(2,2-Dibromo-vinyl)-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-2-(2-methoxy-ethoxymethoxy)-ethoxymethyl]-benzene (155853-16-0) → [(S)-2-[(1R,2R,4S)-2-Ethynyl-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-2-(2-methoxy-ethoxymethoxy)-ethoxymethyl]-benzene + {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane (155853-18-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tert-butyl[(1S)-4-iodo-1-methylbutoxy]dimethylsilane; In tetrahydrofuran; at -78 ℃; Yields of byproduct given;

DOI:10.1039/c39940000483

Reference yield:

benzyl bromide (100-39-0) → {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane (155853-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / tetrahydrofuran; dimethylformamide / Ambient temperature

2: Bu₄NF / tetrahydrofuran / Ambient temperature

3: K₂CO₃ / methanol / Ambient temperature

4: 1.) BuLi / 1.) THF, -78 deg C, 1h, 2.) THF, a) -78 deg C, 1 h, b) RT, 1 h

5: iPr₂NEt / 1,2-dichloro-ethane / 50 °C

6: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, RT

7: SmI₂, HMPA / tetrahydrofuran / Ambient temperature

8: K₂CO₃ / methanol / Ambient temperature

9: Ph₃P / CH₂Cl₂ / 0 °C

10: 1.) BuLi, 2.) HMPA / 2.) THF, -78 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; samarium diiodide; dimethylsulfide; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/c39940000483

Reference yield:

(1S,2R,4R)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentanecarbaldehyde (135191-50-3,135269-24-8) → {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane (155853-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / Ambient temperature

2: Ph₃P / CH₂Cl₂ / 0 °C

3: 1.) BuLi, 2.) HMPA / 2.) THF, -78 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium carbonate; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1039/c39940000483

upstream raw materials:

tert-butyl[(1S)-4-iodo-1-methylbutoxy]dimethylsilane

[(S)-2-[(1R,2R,4S)-2-(2,2-Dibromo-vinyl)-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-2-(2-methoxy-ethoxymethoxy)-ethoxymethyl]-benzene

(R)-5-(chloromethyl)tetrahydro-2-furanone

(2S)-2-methylbutane-1,4-diol