(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

Base Information

Chemical Name:(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate
CAS No.:256343-63-2
Molecular Formula:C₂₃H₂₈O₆S
Molecular Weight:432.538
Hs Code.:

Synonyms:(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

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Chemical Property of (3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

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Technology Process of (3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

There total 5 articles about (3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate 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: 75.0%

: 882-33-7
diphenyldisulfane

: 256343-62-1
(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4''-yl)-3'-(2'-furyl)]propyl acetoacetate

: 256343-63-2
(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

Guidance literature:: (3'R,4''S)-methyl 2-[3'-(2"-dimethyl-1",3"-dioxolan-4''-yl)-3'-(2"'-furyl)]propyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

With n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 1.5h;

diphenyldisulfane; In tetrahydrofuran; hexane; at -15 - 20 ℃;
DOI:10.1016/S0040-4020(99)00882-0

Reference yield:

: 64520-58-7,917877-01-1
ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 256343-63-2
(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 2 h / -78 °C

2.1: 3.78 g / LiAlH₄ / tetrahydrofuran / 6 h / Heating

3.1: TsCl; pyridine

3.2: 85 percent / NaI

4.1: NaH / tetrahydrofuran / 1 h / 0 °C

4.2: 90 percent / tetrahydrofuran / 27 h / Heating

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

5.3: 75 percent / tetrahydrofuran; hexane / -15 - 20 °C

With pyridine; lithium aluminium tetrahydride; sodium hydride; p-toluenesulfonyl chloride; In tetrahydrofuran; diethyl ether; 1.1: Addition / 2.1: Reduction / 3.1: Tosylation / 3.2: Iodination / 4.1: Metallation / 4.2: Alkylation / 5.1: Metallation / 5.2: Metallation / 5.3: Substitution;
DOI:10.1016/S0040-4020(99)00882-0

Reference yield:

: 256343-60-9
(3R,4'S)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-(2-furyl)-propanol

: 256343-63-2
(3'R,4''S)-methyl 2-[3'-(2-dimethyl-1,3-dioxolan-4-yl)-3'-(2'-furyl)]propyl-4-phenylthio-acetoacetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: TsCl; pyridine

1.2: 85 percent / NaI

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 27 h / Heating

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

3.3: 75 percent / tetrahydrofuran; hexane / -15 - 20 °C

With pyridine; sodium hydride; p-toluenesulfonyl chloride; In tetrahydrofuran; 1.1: Tosylation / 1.2: Iodination / 2.1: Metallation / 2.2: Alkylation / 3.1: Metallation / 3.2: Metallation / 3.3: Substitution;
DOI:10.1016/S0040-4020(99)00882-0