(S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one

Base Information

• Chemical Name: (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one
• CAS No.: 150369-16-7
• Molecular Formula: C₄₃H₄₅O₅P
• Molecular Weight: 672.801

Synonyms:(S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one

Chemical Property of (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one

Chemical Property:

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Technology Process of (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one

There total 15 articles about (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one 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: 67.0%

(S)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-thiobutyric acid S-phenyl ester (150369-03-2) + Methylenetriphenylphosphorane (19493-09-5) → (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ5-phosphanylidene)-pentan-2-one (150369-16-7)

Guidance literature:

In toluene; at 110 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)73673-2

Reference yield:

benzyl bromide (100-39-0) → (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ5-phosphanylidene)-pentan-2-one (150369-16-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH

2: DIBAlH

3: 93 percent / Swern oxidation

4: 1.) NaH / 1.) THF

5: 73 percent / TMSCl / tetrahydrofuran / -75 - -40 °C

6: 1.) NaOH, 30percent H₂O₂, 2.) HCl

7: 1.) PhOP(O)Cl₂

8: 67 percent / toluene / 1.5 h / 110 °C

With hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; O-phenyl phosphorodichloridate; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)73673-2

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ5-phosphanylidene)-pentan-2-one (150369-16-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 3 Angstroem sieves / methanol / 40 h / 20 °C

2: imidazole

4: Bu₃SnH

5: Bu₄NF / tetrahydrofuran

6: 1.) NaH

7: DIBAlH

8: 93 percent / Swern oxidation

9: 1.) NaH / 1.) THF

10: 73 percent / TMSCl / tetrahydrofuran / -75 - -40 °C

11: 1.) NaOH, 30percent H₂O₂, 2.) HCl

12: 1.) PhOP(O)Cl₂

13: 67 percent / toluene / 1.5 h / 110 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane; 3 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; O-phenyl phosphorodichloridate; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/S0040-4039(00)73673-2

upstream raw materials:

(S)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-thiobutyric acid S-phenyl ester

Methylenetriphenylphosphorane

benzyl bromide

4-methoxy-benzaldehyde

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