4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol
CAS No.:370593-31-0
Molecular Formula:C₂₃H₂₉IO₄Si
Molecular Weight:524.471
Hs Code.:

4-(<i>tert</i>-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2<i>H</i>-pyran-3-ol

Synonyms:4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

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Chemical Property of 4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

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Technology Process of 4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

There total 6 articles about 4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol 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:

: 4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-iodo-2-methyl-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester

: 370593-31-0
4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: 4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-iodo-2-methyl-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester; With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃;

With sodium tetrahydroborate; ethanol; In diethyl ether; hexane; at 0 ℃; for 1h; Further stages.;
DOI:10.1021/ol0161357

Reference yield:

: 200421-45-0
(S)-2-methyl-4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester

: 370593-31-0
4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 29 percent / benzene / 36 h / Heating

2.1: 0.65 g / DBU; pyridine / CH₂Cl₂ / 6 h / Heating

3.1: 81 percent / I₂; pyridine / CH₂Cl₂ / 5 h / 23 °C

4.1: CeCl₃*7H₂O; NaBH₄ / ethanol; CH₂Cl₂ / 2 h / -78 - 0 °C

4.2: 64 percent / K₂CO₃ / aq. ethanol / 3 h / 23 °C

5.1: imidazole / dimethylformamide / 48 h / 23 °C

6.1: DIBAL-H / diethyl ether; hexane / -78 °C

6.2: 0.276 g / EtOH; NaBH₄ / diethyl ether; hexane / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; iodine; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol0161357

Reference yield:

: 370593-27-4
(2S,3S)-3-Acetoxy-2-methyl-4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester

: 370593-31-0
4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxymethyl-5-iodo-2-methyl-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 0.65 g / DBU; pyridine / CH₂Cl₂ / 6 h / Heating

2.1: 81 percent / I₂; pyridine / CH₂Cl₂ / 5 h / 23 °C

3.1: CeCl₃*7H₂O; NaBH₄ / ethanol; CH₂Cl₂ / 2 h / -78 - 0 °C

3.2: 64 percent / K₂CO₃ / aq. ethanol / 3 h / 23 °C

4.1: imidazole / dimethylformamide / 48 h / 23 °C

5.1: DIBAL-H / diethyl ether; hexane / -78 °C

5.2: 0.276 g / EtOH; NaBH₄ / diethyl ether; hexane / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; iodine; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0161357