[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Base Information

Chemical Name:[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde
CAS No.:867033-49-6
Molecular Formula:C₂₁H₂₉IO₅
Molecular Weight:488.363
Hs Code.:

Synonyms:[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

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Chemical Property of [(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

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Technology Process of [(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

There total 7 articles about [(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde 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%

: 867033-65-6
2-[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol

: 867033-49-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol051584i

Reference yield:

: 867033-61-2
tert-Butyl-{2-[(2R,4R,5S)-2-((E)-2-iodo-1-methyl-vinyl)-5-methyl-6-methylene-[1,3]dioxan-4-yl]-ethoxy}-diphenyl-silane

: 867033-49-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / Me₂AlCl / CH₂Cl₂; hexane / -78 - 0 °C

2.1: LiHMDS / tetrahydrofuran / -78 - -20 °C

2.2: 68 percent / HMPA / tetrahydrofuran / 2 h / -20 °C

3.1: 81 percent / NaBH₄ / ethanol / 0.5 h / -10 °C

4.1: 92 percent / 15-crown-5; KH / tetrahydrofuran / 0.17 h / 0 - 65 °C

5.1: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

6.1: 92 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; 15-crown-5; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; dimethylaluminum chloride; potassium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ol051584i

Reference yield:

: 867033-54-3
(2R,3S,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-((E)-2-iodo-1-methyl-vinyl)-3-methyl-tetrahydro-pyran-4-one

: 867033-49-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiHMDS / tetrahydrofuran / -78 - -20 °C

1.2: 68 percent / HMPA / tetrahydrofuran / 2 h / -20 °C

2.1: 81 percent / NaBH₄ / ethanol / 0.5 h / -10 °C

3.1: 92 percent / 15-crown-5; KH / tetrahydrofuran / 0.17 h / 0 - 65 °C

4.1: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

5.1: 92 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; 15-crown-5; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ol051584i