(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

Base Information

Chemical Name:(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan
CAS No.:583826-62-4
Molecular Formula:C₂₆H₃₅IO₅
Molecular Weight:554.465
Hs Code.:

Synonyms:(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

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Chemical Property of (2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

Chemical Property:

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Technology Process of (2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

There total 8 articles about (2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan 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: 84.0%

: 583826-61-3
((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-diisopropoxymethyl-tetrahydro-furan-2-yl)-methanol

: 583826-62-4
(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 80 ℃; for 1h;
DOI:10.1016/S0040-4039(03)00844-X

Reference yield:

: 583826-59-9
((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-thiazol-2-yl-tetrahydro-furan-2-yl)-methanol

: 583826-62-4
(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; DMAP / 24 h / 20 °C

2.1: acetonitrile / 0.25 h / 20 °C

3.1: NaBH₄; MeOH / 0.08 h / 20 °C

3.2: AgNO₃; H₂O / acetonitrile / 0.17 h / 20 °C

4.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / 20 °C

5.1: Bu₄NF / tetrahydrofuran / 2 h / 20 °C

6.1: 84 percent / iodine; triphenylphosphine; imidazole / toluene / 1 h / 80 °C

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(03)00844-X

Reference yield:

: 583826-57-7
2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-thiazole

: 583826-62-4
(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-diisopropoxymethyl-5-iodomethyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 7 steps

1.1: Ac₂O; AcOH; H₂SO₄ / 1 h / 20 °C

1.2: 82 percent / Et₃N; aq. MeOH / 18 h / 20 °C

2.1: pyridine; DMAP / 24 h / 20 °C

3.1: acetonitrile / 0.25 h / 20 °C

4.1: NaBH₄; MeOH / 0.08 h / 20 °C

4.2: AgNO₃; H₂O / acetonitrile / 0.17 h / 20 °C

5.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / 20 °C

6.1: Bu₄NF / tetrahydrofuran / 2 h / 20 °C

7.1: 84 percent / iodine; triphenylphosphine; imidazole / toluene / 1 h / 80 °C

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; acetic anhydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(03)00844-X