(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

Base Information

Chemical Name:(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde
CAS No.:536738-08-6
Molecular Formula:C₂₁H₄₄O₄Si₂
Molecular Weight:416.749
Hs Code.:

Synonyms:(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

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Chemical Property of (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

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Technology Process of (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

There total 1 articles about (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde 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

: 536738-08-6
(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 536738-08-6
(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

: 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 7 steps

1: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

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

3: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

4: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

5: 82 percent / KH / tetrahydrofuran / 2 h / Heating

6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7: 84 percent / HCl / diethyl ether / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; ethylene glycol; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Tsuchihashi-Suzuki rearrangement;
DOI:10.1021/ja034332q

Reference yield:

: 536738-08-6
(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-triisopropylsilanyloxy-ethyl]-2-methyl-oxirane-2-carbaldehyde

: 536738-12-2
(2R,3R,4S)-4-[1,3]Dioxolan-2-yl-3-(4-methoxy-benzyloxy)-4,5-dimethyl-hex-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

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

3: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

4: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

5: 82 percent / KH / tetrahydrofuran / 2 h / Heating

6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; ethylene glycol; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Tsuchihashi-Suzuki rearrangement;
DOI:10.1021/ja034332q