(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

Base Information

Chemical Name:(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one
CAS No.:941295-88-1
Molecular Formula:C₁₆H₂₂O₅
Molecular Weight:294.348
Hs Code.:

Synonyms:(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

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Chemical Property of (-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

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Technology Process of (-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

There total 8 articles about (-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-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: 95.0%

: 941295-78-9
(+)-(1R,2S)-2-(benzyloxy)-1-[(2R,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-ol

: 941295-88-1
(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 8.5h;
DOI:10.1021/ol070405p

Reference yield:

: 941295-59-6
(-)-(S)-2-(benzyloxy)-7,7-dimethoxyhept-4-yn-3-one

: 941295-88-1
(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: LiAlH₄ / CH₂Cl₂ / 1 h / -78 °C

2: 99 percent / Red-Al / diethyl ether; toluene / 0 - 20 °C

3: D-diethyl tartrate; tert-butyl hydroperoxide / Ti(Oi-Pr)4 / CH₂Cl₂; decane / 72 h / -4 °C

4: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; Diethyl tartrate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; In diethyl ether; decane; dichloromethane; toluene; 3: Sharpless epoxidation;
DOI:10.1021/ol070405p

Reference yield:

: 941295-62-1
(+)-(2S,3S)-2-(benzyloxy)-7,7-dimethoxyhept-4-yn-3-ol

: 941295-88-1
(-)-(S)-2-(benzyloxy)-1-[(2S,3R)-3-(2,2-dimethoxyethyl)oxiran-2-yl]propan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / Red-Al / diethyl ether; toluene / 0 - 20 °C

2: D-diethyl tartrate; tert-butyl hydroperoxide / Ti(Oi-Pr)4 / CH₂Cl₂; decane / 72 h / -4 °C

3: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With tert.-butylhydroperoxide; Diethyl tartrate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; In diethyl ether; decane; dichloromethane; toluene; 2: Sharpless epoxidation;
DOI:10.1021/ol070405p