(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

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Chemical Name:(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol
CAS No.:874660-46-5
Molecular Formula:C₃₇H₅₈O₆Si
Molecular Weight:626.949
Hs Code.:

Synonyms:(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

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Chemical Property of (R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

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Technology Process of (R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

There total 16 articles about (R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-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: 80.0%

: 874660-45-4
(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde

: 1826-67-1
vinyl magnesium bromide

: 874660-46-5
(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 0.0833333h; optical yield given as %de;
DOI:10.1002/chem.200900776

Reference yield:

: 874660-45-4
(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde

: 593-60-2,25951-54-6
Vinyl bromide

: 874660-46-5
(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

Guidance literature:: Vinyl bromide; With iodine; magnesium; In tetrahydrofuran; at 0 - 20 ℃;

(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/ol0526625

Reference yield:

: 874660-41-0
(R)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,3-diol

: 874660-46-5
(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: 96 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 1 h

3.1: 95 percent / tetrahydrofuran; diethyl ether / -78 °C

4.1: 73 percent / sodium hydride / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: triethylamine / tetrahydrofuran / -78 - 0 °C

6.1: n-butyl lithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: 40 g / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

7.1: sodium (trimethylsilyl)amide / tetrahydrofuran; toluene / -78 - -65 °C

7.2: tetrahydrofuran; toluene / 0.25 h

8.1: 200 mg / lithium borohydride / methanol; tetrahydrofuran / 1 h / 0 °C

9.1: pyridine; Dess-Martin periodinane / CH₂Cl₂ / 0.75 h

10.1: magnesium; iodine / tetrahydrofuran / 0 - 20 °C

10.2: 146 mg / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; sodium bis(trimethylsilyl)amide; iodine; sodium hydride; Dess-Martin periodane; magnesium; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0526625