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

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Chemical Name: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
CAS No.:867033-65-6
Molecular Formula:C₂₁H₃₁IO₅
Molecular Weight:490.379
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 97.0%

: 867033-55-4
tert-Butyl-{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]-ethoxy}-diphenyl-silane

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
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

: 867033-65-6
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

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; 15-crown-5; tetrabutyl ammonium fluoride; dimethylaluminum chloride; potassium hydride; 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

: 867033-65-6
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

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; 15-crown-5; tetrabutyl ammonium fluoride; potassium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;
DOI:10.1021/ol051584i