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

Base Information

Chemical Name:2-[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol
CAS No.:380909-84-2
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

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

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

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

There total 4 articles about 2-[(2R,3S,4S,5R,6R)-4-(3,4-Dimethoxy-benzyloxy)-6-ethynyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol 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: 99.0%

: 380909-58-0
(2R,3S,4S,5R,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-6-[(triisopropylsilanyl)-ethynyl]-tetrahydro-pyran

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 99 percent / TBAF / tetrahydrofuran / 1.5 h

With tetrabutyl ammonium fluoride; potassium hydride; 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

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

Guidance literature:: Multi-step reaction with 4 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

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