(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

Base Information

Chemical Name:(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol
CAS No.:625822-04-0
Molecular Formula:C₂₀H₃₂Cl₂O₄Si
Molecular Weight:435.463
Hs Code.:

Synonyms:(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

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Chemical Property of (2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

There total 9 articles about (2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-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: 94.0%

: 625822-03-9
(2R,3R,4S,5R)-tert-butyl-[5-(2,6-dichlorobenzyloxymethyl)-4-(4-methoxyphenoxymethyl)-3-methyltetrahydrofuran-2-ylmethoxy]dimethylsilane

: 625822-04-0
(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 3h; pH=7;
DOI:10.1021/ol030101c DOI:10.1021/jo062396o

Reference yield:

: 88424-95-7
2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol

: 625822-04-0
(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / NaH / dimethylformamide

2.1: 85 percent / p-TsOH / methanol

3.1: 92 percent / NaH; n-Bu₄NI / dimethylformamide / 20 °C

4.1: 87 percent / iodine / acetonitrile / 3 h / -20 °C

5.1: cesium trifluoroacetate / dimethylformamide / 36 h / 90 °C

5.2: 92 percent / diethylamine / dimethylformamide / 3 h / 20 °C

6.1: 95 percent / imidazole / dimethylformamide / 20 °C

7.1: 94 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C / pH 7

With 1H-imidazole; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; cesium trifluoroacetate; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo062396o

Reference yield:

: 625822-01-7
(2R,3S,4R,5R)-2-(2,6-dichlorobenzyloxymethyl)-5-iodomethyl-3-(4-methoxybenzyloxy)-4-methyltetrahydrofuran

: 625822-04-0
(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: cesium trifluoroacetate / dimethylformamide / 36 h / 90 °C

1.2: 92 percent / diethylamine / dimethylformamide / 3 h / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 20 °C

3.1: 94 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C / pH 7

With 1H-imidazole; cesium trifluoroacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo062396o