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

Base Information

Chemical Name:((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-thiazol-2-yl-tetrahydro-furan-2-yl)-methanol
CAS No.:583826-59-9
Molecular Formula:C₂₂H₂₃NO₄S
Molecular Weight:397.495
Hs Code.:

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

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Chemical Property of ((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-thiazol-2-yl-tetrahydro-furan-2-yl)-methanol

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Technology Process of ((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-thiazol-2-yl-tetrahydro-furan-2-yl)-methanol

There total 2 articles about ((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-thiazol-2-yl-tetrahydro-furan-2-yl)-methanol 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: 82.0%

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

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

Guidance literature:: 2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-thiazole; With sulfuric acid; acetic anhydride; acetic acid; at 20 ℃; for 1h;

With methanol; triethylamine; at 20 ℃; for 18h;
DOI:10.1016/S0040-4039(03)00844-X

Reference yield:

: Acetic acid (3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-thiazol-2-yl-tetrahydro-furan-2-yl ester

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 60 percent / samarium(II) iodide; ethylene glycol / tetrahydrofuran / 0.5 h / 20 °C

2.1: Ac₂O; AcOH; H₂SO₄ / 1 h / 20 °C

2.2: 82 percent / Et₃N; aq. MeOH / 18 h / 20 °C

With samarium diiodide; sulfuric acid; acetic anhydride; ethylene glycol; acetic acid; In tetrahydrofuran;
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

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

Guidance literature:: Multi-step reaction with 5 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

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