(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Base Information

• Chemical Name: (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate
• CAS No.: 874896-58-9
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Chemical Property of (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Chemical Property:

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Technology Process of (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

There total 10 articles about (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 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: 92.0%

(4S,Z)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (1061228-25-8) → (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (874896-58-9)

Guidance literature:

With trimethylphosphane; In toluene; tert-butyl alcohol; at 35 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol8018874

Reference yield: 80.0%

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (874896-58-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.07.006

Reference yield: 80.0%

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (4S,Z)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (1061228-25-8) + (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (874896-58-9)

Guidance literature:

In dichloromethane; for 2h;

DOI:10.1021/jo0521192

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

2-O-benzyl-3,4-O-isopropylidene-L-threose

ethyl (triphenylphosphoranylidene)acetate

benzyl bromide

Downstream raw materials:

(S,E)-4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-en-1-ol

(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

ethyl (2S,3R,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate

ethyl (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate

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