tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane
CAS No.:378238-77-8
Molecular Formula:C₂₄H₂₉IO₄Si
Molecular Weight:536.482
Hs Code.:

Synonyms:tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

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Chemical Property of tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

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Technology Process of tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

There total 5 articles about tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-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:

: 378238-90-5
[1-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-meth-(E)-ylidene]-hydrazine

: 378238-77-8
tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

Guidance literature:: [1-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-meth-(E)-ylidene]-hydrazine; With iodine; N,N,N',N'-tetramethylguanidine; In diethyl ether; for 1h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 60 ℃; for 20h; Further stages.;
DOI:10.1021/ol0167210

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 378238-77-8
tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / imidazole / dimethylformamide / 18 h

2.1: AcOH / H₂O / 48 h / 20 °C

2.2: 96 percent / NaIO₄ / H₂O; tetrahydrofuran / 5 h / 20 °C

3.1: 100 percent / hydrazine hydrate / ethanol / 0.5 h / 100 °C

4.1: I₂; 1,1,3,3-tetramethylguanidine / diethyl ether / 1 h

4.2: DBU / toluene / 20 h / 60 °C

With 1H-imidazole; iodine; hydrazine hydrate; acetic acid; N,N,N',N'-tetramethylguanidine; In diethyl ether; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0167210

Reference yield:

: 2595-05-3
Diacetone D-glucose

: 378238-77-8
tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / imidazole / dimethylformamide / 18 h

2.1: AcOH / H₂O / 48 h / 20 °C

2.2: 96 percent / NaIO₄ / H₂O; tetrahydrofuran / 5 h / 20 °C

3.1: 100 percent / hydrazine hydrate / ethanol / 0.5 h / 100 °C

4.1: I₂; 1,1,3,3-tetramethylguanidine / diethyl ether / 1 h

4.2: DBU / toluene / 20 h / 60 °C

With 1H-imidazole; iodine; hydrazine hydrate; acetic acid; N,N,N',N'-tetramethylguanidine; In diethyl ether; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0167210