(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

Base Information

Chemical Name:(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran
CAS No.:625822-08-4
Molecular Formula:C₁₆H₁₉Cl₂IO₂
Molecular Weight:441.136
Hs Code.:

Synonyms:(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

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Chemical Property of (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

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Technology Process of (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

There total 14 articles about (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran 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: 86.0%

: 625822-07-3
(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-2-ethynyl-3-methyltetrahydrofuran

: 74-88-4
methyl iodide

: 625822-08-4
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

Guidance literature:: (2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-2-ethynyl-3-methyltetrahydrofuran; methyl iodide; With n-butyllithium; n-butyl tin hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -65 - 20 ℃;

With iodine; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/ol030101c

Reference yield:

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

: 625822-08-4
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

Guidance literature:: Multi-step reaction with 13 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

8.1: 92 percent / toluene / 3 h / 100 °C

9.1: 96 percent / n-Bu₃SnH; AIBN / toluene / 0.58 h / 100 °C

10.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

11.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: potassium tert-butoxide / tetrahydrofuran; propan-2-ol / 0.08 h / -78 °C

12.2: 79 percent / tetrahydrofuran; propan-2-ol / cooling

13.1: n-Bu₃SnCu(CN)Li / tetrahydrofuran / 0.5 h / -78 °C

13.2: DMPU / tetrahydrofuran / -78 - 20 °C

13.3: 86 percent / iodine / tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); n-Bu₃SnCu(CN)Li; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; cesium trifluoroacetate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 11.1: Swern oxidation;
DOI:10.1021/jo062396o

Reference yield:

: 625822-05-1
(2R,3R,4S,5R)-tert-butyl-[5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethoxy]dimethylsilane

: 625822-08-4
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-2-[(E)-2-iodo-1-methylvinyl]-3-methyltetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

2.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: potassium tert-butoxide / tetrahydrofuran; propan-2-ol / 0.08 h / -78 °C

3.2: 79 percent / tetrahydrofuran; propan-2-ol / cooling

4.1: n-Bu₃SnCu(CN)Li / tetrahydrofuran / 0.5 h / -78 °C

4.2: DMPU / tetrahydrofuran / -78 - 20 °C

4.3: 86 percent / iodine / tetrahydrofuran / 0.5 h / 20 °C

With oxalyl dichloride; n-Bu₃SnCu(CN)Li; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 2.1: Swern oxidation;
DOI:10.1021/jo062396o