(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

Base Information

Chemical Name:(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al
CAS No.:164364-97-0
Molecular Formula:C₂₄H₅₀O₄Si₂
Molecular Weight:458.83
Hs Code.:

Synonyms:(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

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Chemical Property of (2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

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Technology Process of (2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

There total 1 articles about (2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 164364-97-0
(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / DIBAL / -78 °C

2: 80 percent / (+)-DIPT; Ti(O-i-Pr)4; TBHP / MS 4 Angstroem / CH₂Cl₂ / 6 h / -20 °C

3: TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

4: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

6: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-(+)-diisopropyl tartrate; MS 4 Angstroem; titanium tetrachloride; diisobutylaluminium hydride; MS 4 Angstroem; In tetrahydrofuran; dichloromethane; 4: Sharpless asymmetric epoxidation / 8: Tsuchihashi-Suzuki rearrangement;
DOI:10.1021/ja034332q

Reference yield:

: 164364-97-0
(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

: (2S,3R,4R,5R)-3-[(2R,3R)-2,3-dihydroxy-2-pentyl]-5-(triisopropylsiloxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyloxolane

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

2: 82 percent / KH / tetrahydrofuran / 2 h / Heating

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4: 84 percent / HCl / diethyl ether / 2 h / 20 °C

5: 98 percent / DMAP; imidazole / CH₂Cl₂ / 20 °C

6: 85 percent / NMO; aq. OsO₄ / acetone / 4 h / 20 °C

7: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 0 °C

8: tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; ethylene glycol; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 7: Swern oxidation;
DOI:10.1021/ja034332q

Reference yield:

: 164364-97-0
(2S,3R,4R)-2-methyl-2-(2-propenyl)-4-O-(tert-butyldimethylsiloxy)-5-O-(triisopropylsiloxy)-3-hydroxy-pentan-1-al

: 536737-61-8
(2S,3S,4R,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)oxolane

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

2: 82 percent / KH / tetrahydrofuran / 2 h / Heating

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4: 84 percent / HCl / diethyl ether / 2 h / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; potassium hydride; ethylene glycol; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja034332q