{(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane

Base Information

• Chemical Name: {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane
• CAS No.: 781651-85-2
• Molecular Formula: C₃₀H₅₂O₃Si
• Molecular Weight: 488.827
• Mol file: 781651-85-2.mol

Synonyms:{(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane

Chemical Property of {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane

There total 13 articles about {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-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: 100.0%

(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol (781652-08-2) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane (781651-85-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.200460434

Reference yield: 70.0%

((E)-(R)-1-Benzyloxymethyl-but-2-enyl)-dimethyl-phenyl-silane + Acetic acid (3S,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl ester (781651-86-3) → (R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol (781652-08-2) + {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane (781651-85-2)

Guidance literature:

With titanium(IV) trichloride isopropoxide; In dichloromethane; at -78 ℃;

DOI:10.1002/anie.200460434

Reference yield:

(2R,3R)-3-((R)-1-Methyl-2-triisopropylsilanyloxy-ethyl)-oxirane-2-carbaldehyde → {(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane (781651-85-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tBuOK / tetrahydrofuran / -78 °C

2.1: dimethylformamide / 0 °C

3.1: H₂ / PtO₂ / ethanol / 20 °C

3.2: 89 percent / Ti(OiPr)4 / dimethylformamide / 100 °C

4.1: DIBAL-H / CH₂Cl₂ / -78 °C

5.1: pyridine; DMAP / -78 - 20 °C

6.1: 11 percent / TiCl₃(OiPr) / CH₂Cl₂ / -78 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; titanium(IV) trichloride isopropoxide; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Horner-Emmons reaction;

DOI:10.1002/anie.200460434

upstream raw materials:

Acetic acid (3S,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl ester

(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

triisopropylsilyl trifluoromethanesulfonate

[(2S,3R)-3-((R)-1-Methyl-2-triisopropylsilanyloxy-ethyl)-oxiranyl]-methanol

Downstream raw materials:

zincophorin