(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Base Information

Chemical Name:(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile
CAS No.:375826-87-2
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:

Synonyms:(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Chemical Property of (R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Technology Process of (R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

There total 7 articles about (R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile 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: 80.0%

: 151-50-8
potassium cyanide

: 77-76-9
2,2-dimethoxy-propane

: 375826-95-2
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

: 375826-87-2
(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multistep reaction;
DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D

Reference yield:

: 233681-54-4
(2R,3S)-3-benzyloxy-2,4-dimethylpentanal

: 375826-87-2
(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: acetonitrile / 90 °C

2: 88 percent / DIBAL-H

3: 99 percent / o-iodoxybenzoic acid / dimethylsulfoxide

4: Sn(OTf)2; N-ethylpiperidine / CH₂Cl₂ / -50 °C

5: 90 percent / imidazole

With 1-ethyl-piperidine; 1H-imidazole; tin(II) trifluoromethanesulfonate; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Wittig reaction;
DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D

Reference yield:

: 375826-91-8
(2S,3S)-3-Benzyloxy-2,4-dimethyl-pentan-1-ol

: 375826-87-2
(R)-6-((E)-(3S,4S)-4-Benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 7 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

2: acetonitrile / 90 °C

3: 88 percent / DIBAL-H

4: 99 percent / o-iodoxybenzoic acid / dimethylsulfoxide

5: Sn(OTf)2; N-ethylpiperidine / CH₂Cl₂ / -50 °C

6: 90 percent / imidazole

With 1-ethyl-piperidine; 1H-imidazole; tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Swern oxidation / 2: Wittig reaction;
DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D