(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

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Chemical Name:(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester
CAS No.:849482-40-2
Molecular Formula:C₃₁H₅₂O₆Si
Molecular Weight:548.836
Hs Code.:

Synonyms:(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

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Chemical Property of (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

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Technology Process of (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

There total 17 articles about (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester 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: 98.0%

: 849482-22-0
(3R,5R)-5-Benzyloxymethoxy-hept-1-en-3-ol

: 849482-25-3
(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid

: 849482-40-2
(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

Guidance literature:: (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

(3R,5R)-5-Benzyloxymethoxy-hept-1-en-3-ol; With dmap; In benzene; at 20 ℃; for 2h;
DOI:10.1021/ol0500160

Reference yield:

: 849482-33-3
(3R,5S)-5-Benzyloxy-hexane-1,3-diol

: 849482-40-2
(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / Et₃N / CH₂Cl₂ / 8 h / 0 °C

2.1: 74 percent / PPTS / benzene / 4 h / Heating

3.1: 85 percent / NaI / acetone / 3 h / Heating

4.1: 92 percent / n-Bu₃SnH; Et₃B / toluene; hexane / 1 h / -78 °C

5.1: 86 percent / H₂ / Pd/C / methanol / 0.5 h

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 20 °C

7.1: 98 percent / LiOH*H₂O / methanol; H₂O / 5 h / 20 °C

8.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

8.2: 98 percent / DMAP / benzene / 2 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; triethyl borane; 2,4,6-trichlorobenzoyl chloride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; benzene; 8.1: Yamaguchi esterification;
DOI:10.1021/ol0500160

Reference yield:

: 849482-18-4
((2S,4S,6S)-6-Methyl-2-phenyl-[1,3]dioxan-4-yl)-acetic acid tert-butyl ester

: 849482-40-2
(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 80 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

2.1: 95 percent / Et₃N / CH₂Cl₂ / 8 h / 0 °C

3.1: 74 percent / PPTS / benzene / 4 h / Heating

4.1: 85 percent / NaI / acetone / 3 h / Heating

5.1: 92 percent / n-Bu₃SnH; Et₃B / toluene; hexane / 1 h / -78 °C

6.1: 86 percent / H₂ / Pd/C / methanol / 0.5 h

7.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 20 °C

8.1: 98 percent / LiOH*H₂O / methanol; H₂O / 5 h / 20 °C

9.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

9.2: 98 percent / DMAP / benzene / 2 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; triethyl borane; 2,4,6-trichlorobenzoyl chloride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; benzene; 9.1: Yamaguchi esterification;
DOI:10.1021/ol0500160