(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

Base Information

Chemical Name:(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate
CAS No.:222986-44-9
Molecular Formula:C₁₉H₂₈O₅Si
Molecular Weight:364.514
Hs Code.:

Synonyms:(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

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Chemical Property of (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

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Technology Process of (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

There total 11 articles about (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate 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: 95.0%

: 222986-42-7
(2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate

: 222986-44-9
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; at -78 - 0 ℃; for 1.5h;
DOI:10.1016/S0008-6215(00)00031-8

Reference yield:

: 1487-18-9
(furan-2-yl)ethylene

: 222986-44-9
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: (DHQD)2PHAL; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

2: 91 percent / Et₃N / DMAP / CH₂Cl₂ / 6 h / 0 °C

3: 95 percent / NBS; NaHCO₃; NaOAc*3H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 60 percent / Et₃N / DMAP / CH₂Cl₂ / 3 h / -78 °C

5: 95 percent / NaBH₄; CeCl₃ / CH₂Cl₂; methanol / 1.5 h / -78 - 0 °C

With sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; sodium acetate; sodium hydrogencarbonate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); dmap; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 1: Oxidation / 2: Alkylation / 3: Oxidation / 4: Acylation / 5: Reduction;
DOI:10.1016/S0008-6215(00)00031-8

Reference yield:

: 14086-08-9
(R)-2-(2-furyl)-1,2-ethanediol

: 222986-44-9
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / Et₃N / DMAP / CH₂Cl₂ / 6 h / 0 °C

2: 95 percent / NBS; NaHCO₃; NaOAc*3H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

3: 60 percent / Et₃N / DMAP / CH₂Cl₂ / 3 h / -78 °C

4: 95 percent / NaBH₄; CeCl₃ / CH₂Cl₂; methanol / 1.5 h / -78 - 0 °C

With sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; sodium acetate; sodium hydrogencarbonate; triethylamine; dmap; In tetrahydrofuran; methanol; dichloromethane; water; 1: Alkylation / 2: Oxidation / 3: Acylation / 4: Reduction;
DOI:10.1016/S0008-6215(00)00031-8