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

Base Information

Chemical Name:2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-thiazole
CAS No.:583826-57-7
Molecular Formula:C₂₉H₂₉NO₄S
Molecular Weight:487.62
Hs Code.:

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

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

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

There total 1 articles about 2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-thiazole 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: 60.0%

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

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

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

Guidance literature:: With samarium diiodide; ethylene glycol; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4039(03)00844-X

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:

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

: C₅₃H₆₂O₉

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetonitrile / 0.25 h / 20 °C

2.1: NaBH₄ / methanol / 0.08 h / 20 °C

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

3.1: butyllithium; 4 Angstroem molecular sieves / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -20 °C

With sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile; 3.1: Wittig coupling;
DOI:10.1016/S0040-4039(03)00844-X