(Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Base Information

• Chemical Name: (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol
• CAS No.: 194232-23-0
• Molecular Formula: C₄₇H₉₀O₇Si₂
• Molecular Weight: 823.398
• Mol file: 194232-23-0.mol

Synonyms:(Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Chemical Property of (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

There total 6 articles about (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-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:

1-((Z)-(2R,3R,4S,5S,10R,11S,12R)-13-Benzyloxy-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-5,11-bis-triisopropylsilanyloxy-tridec-8-enyloxymethyl)-4-methoxy-benzene → (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol (194232-23-0)

Guidance literature:

With hydrogen; nickel; In ethanol; Yield given;

DOI:10.1021/jo9708093

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol (194232-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TEA

2: H₂ / Ra/Ni / ethanol

With TEA; hydrogen; nickel; In ethanol;

DOI:10.1021/jo9708093

Reference yield:

[(Z)-(1S,2R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-5-iodo-2,4-dimethyl-pent-3-enyloxy]-triisopropyl-silane (153628-63-8) → (Z)-(2R,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol (194232-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) lithium hexamethyldisilazide, tetramethylethylenediamine / 1) THF, hexane, -78 deg C

2: LiAlH₄, LiI / diethyl ether / -78 °C

3: TEA

4: H₂ / Ra/Ni / ethanol

With lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; TEA; hydrogen; lithium iodide; lithium hexamethyldisilazane; nickel; In diethyl ether; ethanol;

DOI:10.1021/jo9708093

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

[(Z)-(1S,2R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-5-iodo-2,4-dimethyl-pent-3-enyloxy]-triisopropyl-silane

(Z)-(2R,3R,4S,10R,11S,12R)-13-Benzyloxy-1-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-11-triisopropylsilanyloxy-tridec-8-en-5-one

Downstream raw materials:

1-((8Z,13Z)-(2R,3R,4S,5S,6R,10R,11S,12R)-14-Iodo-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-5,11-bis-triisopropylsilanyloxy-tetradeca-8,13-dienyloxymethyl)-4-methoxy-benzene

(Z)-(2S,3S,4R,8R,9S,10S,11R,12R)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-enal