[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

Base Information

Chemical Name:[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane
CAS No.:213912-96-0
Molecular Formula:C₂₀H₃₁IO₃Si
Molecular Weight:474.454
Hs Code.:

Synonyms:[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

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Chemical Property of [2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

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Technology Process of [2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

There total 10 articles about [2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane 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:

: 3020-28-8
(iodomethyl)triphenylphosphonium iodide

: 1054677-24-5
(2R,3S)-3-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxetane-3-carbaldehyde

: 213912-96-0
[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 220325-36-0
(3aR,5R,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>dihydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6(5H)-one

: 213912-96-0
[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 7 steps

1.1: diethyl ether; tetrahydrofuran / 0.33 h / -78 °C

2.1: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

3.1: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

4.2: 76 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 74 percent / potassium hexamethyldisilazide; N-phenyltriflimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.1: OsO₄; NMO; NaIO₄ / tetrahydrofuran; H₂O / 23.5 h / pH 7

7.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; N,N-phenylbistrifluoromethane-sulfonimide; sodium hexamethyldisilazane; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Addition / 2.1: Alkylation / 3.1: deacetalization / 4.1: Oxidation / 4.2: Reduction / 5.1: Cyclization / 6.1: Oxidation / 7.1: Wittig condensation;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 189165-94-4
(3aR,5R,6S,6aR)-5-<2-(tert-butyldimethylsiloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-ol

: 213912-96-0
[2-{(2R,3S)-3-(benzyloxy)-3-[(Z)-2-iodovinyl]-2-oxetanyl}ethoxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 8 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 0.33 h / -78 °C

3.1: 96 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide; tetrahydrofuran / 0 - 20 °C

4.1: 81 percent / TiCl₄ / CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

5.2: 76 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 74 percent / potassium hexamethyldisilazide; N-phenyltriflimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: OsO₄; NMO; NaIO₄ / tetrahydrofuran; H₂O / 23.5 h / pH 7

8.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; N,N-phenylbistrifluoromethane-sulfonimide; sodium hexamethyldisilazane; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Oxidation / 2.1: Addition / 3.1: Alkylation / 4.1: deacetalization / 5.1: Oxidation / 5.2: Reduction / 6.1: Cyclization / 7.1: Oxidation / 8.1: Wittig condensation;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2