(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Base Information

Chemical Name:(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate
CAS No.:874896-60-3
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

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Chemical Property of (4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

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Technology Process of (4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

There total 8 articles about (4R,Z)-methyl 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: 82.0%

: 67-56-1
methanol

: 1061228-21-4
(4R,Z)-4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enal

: 874896-60-3
(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Guidance literature:: With sodium cyanide; manganese(IV) oxide; acetic acid; at 25 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol8018874

Reference yield: 80.0%

: 88738-78-7
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

: 104322-68-1
(2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

: 874896-60-3
(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

: methyl (4R,5S)-4-O-benzyl-5,6-O-isopropylidene-4,5,6-trihydroxyhex-2-E-enoate

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;
DOI:10.1021/jo0521192

Reference yield:

: 874897-00-4
(S)-(2-Chloro-acetoxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid ethyl ester

: 874896-60-3
(4R,Z)-methyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / triethylamine; ethanol

2: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating

3: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C

4: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 80 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

With lithium borohydride; oxalyl dichloride; 18-crown-6 ether; ethanol; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 4: Swern oxidation / 5: Horner-Emmons reaction;
DOI:10.1021/jo0521192