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

Base Information

Chemical Name:(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate
CAS No.:222986-50-7
Molecular Formula:C₂₂H₃₂O₇Si
Molecular Weight:436.577
Hs Code.:

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

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

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

There total 10 articles about (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-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: 81.0%

: 541-41-3
chloroformic acid ethyl ester

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

: 222986-50-7
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: With pyridine; dmap; In dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1016/S0008-6215(00)00031-8

Reference yield: 80.0%

: 541-41-3
chloroformic acid ethyl ester

: benzoic acid 6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl ester

: 222986-50-7
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: In pyridine;
DOI:10.1021/jo990410+

Reference yield:

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

: 222986-50-7
(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate

Guidance literature:: Multi-step reaction with 6 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

6: 81 percent / pyridine / DMAP / CH₂Cl₂ / 3 h / -78 - 0 °C

With pyridine; 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 / 6: Acylation;
DOI:10.1016/S0008-6215(00)00031-8