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

Base Information

Chemical Name: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
CAS No.:867033-55-4
Molecular Formula:C₃₇H₄₉IO₅Si
Molecular Weight:728.783
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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%

: 867033-63-4
(2R,3R,4S,5R,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-4-ol

: 7306-46-9
4-chloromethyl-1,2-dimethoxy-benzene

: 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

: 93-03-8
(3,4-dimethoxyphenyl)methanol

Guidance literature:: (2R,3R,4S,5R,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-4-ol; 4-chloromethyl-1,2-dimethoxy-benzene; With potassium hydride; 18-crown-6 ether; In tetrahydrofuran; at 0 - 65 ℃; for 0.166667h;

With water; ammonium chloride; In tetrahydrofuran; at 0 ℃;

Reference yield: 92.0%

: 867033-63-4
(2R,3R,4S,5R,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-4-ol

: 7306-46-9
4-chloromethyl-1,2-dimethoxy-benzene

: 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

Guidance literature:: With 15-crown-5; potassium hydride; In tetrahydrofuran; at 0 - 65 ℃; for 0.166667h;
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

: 867033-55-4
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

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; 15-crown-5; dimethylaluminum chloride; potassium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ol051584i