[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Base Information

Chemical Name:[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde
CAS No.:380909-54-6
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-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-ethynyl-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-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

There total 5 articles about [(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-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: 94.0%

: 380909-84-2
2-[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol

: 380909-54-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide;
DOI:10.1021/ja011604l

Reference yield:

: 250328-35-9
(2R,3R,4S,5R,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-6-[(triisopropylsilanyl)-ethynyl]-tetrahydro-pyran-4-ol

: 380909-54-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / KH / tetrahydrofuran / 0.5 h / 0 °C

2: 99 percent / TBAF / tetrahydrofuran / 1.5 h

3: 94 percent / SO₃*pyridine; DMSO

With pyridine-SO₃ complex; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; In tetrahydrofuran;
DOI:10.1021/ja011604l

Reference yield:

: (2R,4R,5S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-eth-(E)-ylidene-5-methyl-2-[(triisopropylsilanyl)-ethynyl]-[1,3]dioxane

: 380909-54-6
[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Me₂AlCl / CH₂Cl₂; hexane

2: 91 percent / NaBH₄ / ethanol / 0.5 h / -10 °C

3: 99 percent / KH / tetrahydrofuran / 0.5 h / 0 °C

4: 99 percent / TBAF / tetrahydrofuran / 1.5 h

5: 94 percent / SO₃*pyridine; DMSO

With sodium tetrahydroborate; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; dimethylaluminum chloride; potassium hydride; dimethyl sulfoxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1: Petasis-Ferrier rearrangement;
DOI:10.1021/ja011604l