(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

Base Information

Chemical Name:(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol
CAS No.:870680-72-1
Molecular Formula:C₂₅H₄₀O₆Si
Molecular Weight:464.674
Hs Code.:

Synonyms:(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

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Chemical Property of (1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

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Technology Process of (1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

There total 9 articles about (1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-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:

: 869348-65-2
(S)-1-(4-Methoxy-benzyloxy)-hept-6-en-3-ol

: 870680-72-1
(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / Hoveyda-Grubbs II catalyst / CH₂Cl₂ / Heating

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 850 mg / AD-mix-α; methanesulfonamide; H2O / 2-methyl-propan-2-ol / 0 - 20 °C

4: 100 percent / Hunig's base; TBAI / CH₂Cl₂

5: LiAlH₄ / tetrahydrofuran / -78 - 20 °C

6: 349 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

7: 83 percent / InI; Pd(OAc)2; PPh₃ / HMPA / tetrahydrofuran / 0 - 25 °C

With palladium diacetate; AD-mix-α; lithium aluminium tetrahydride; Hoveyda-Grubbs catalyst second generation; indium iodide; methanesulfonamide; water; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 6: Dess-Martin oxidation;
DOI:10.1021/ol0523493

Reference yield:

: 870680-55-0
(E)-(S)-6-Hydroxy-8-(4-methoxy-benzyloxy)-oct-2-enoic acid ethyl ester

: 870680-72-1
(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 850 mg / AD-mix-α; methanesulfonamide; H2O / 2-methyl-propan-2-ol / 0 - 20 °C

3: 100 percent / Hunig's base; TBAI / CH₂Cl₂

4: LiAlH₄ / tetrahydrofuran / -78 - 20 °C

5: 349 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

6: 83 percent / InI; Pd(OAc)2; PPh₃ / HMPA / tetrahydrofuran / 0 - 25 °C

With palladium diacetate; AD-mix-α; lithium aluminium tetrahydride; indium iodide; methanesulfonamide; water; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 5: Dess-Martin oxidation;
DOI:10.1021/ol0523493

Reference yield:

: 870680-58-3
(S)-2-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-2-methoxymethoxy-ethanol

: 870680-72-1
(1S,2R,3R)-1-{(2S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-tetrahydro-furan-2-yl}-1-methoxymethoxy-3-methyl-5-trimethylsilanyl-pent-4-yn-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 349 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

2: 83 percent / InI; Pd(OAc)2; PPh₃ / HMPA / tetrahydrofuran / 0 - 25 °C

With palladium diacetate; indium iodide; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation;
DOI:10.1021/ol0523493