(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

Base Information

Chemical Name:(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol
CAS No.:679411-92-8
Molecular Formula:C₂₅H₃₈O₇Si
Molecular Weight:478.658
Hs Code.:

Synonyms:(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

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Chemical Property of (1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

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Technology Process of (1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

There total 5 articles about (1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol 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: 90.0%

: 679411-89-3
(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-one]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-one

: 679411-92-8
(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/ja039400n

Reference yield:

: 222986-37-0
(S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol

: 679411-92-8
(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / NaHCO₃; aq. NaOAc; NBS / tetrahydrofuran / 1 h / 0 °C

2: 82 percent / DMAP / CH₂Cl₂ / 1 h / -78 °C

3: 89 percent / Pd₂(DBA)3*CHCl₃; PPh₃ / CH₂Cl₂ / 1 h / 0 °C

4: 90 percent / aq. HF / acetonitrile / 8 h / 0 °C

5: 92 percent / Pd₂(DBA)3*CHCl₃; PPh₃ / CH₂Cl₂ / 6 h / 0 °C

6: 90 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; hydrogen fluoride; sodium acetate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja039400n

Reference yield:

: 302348-82-9
(2S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one

: 679411-92-8
(1'R,5'S,1R,5S)-1-[1'-benzyloxy-5'-methyloxy-1'H-pyran-4'-ol]-5-(tert-butyldimethylsilanyloxymethyl)-1H-pyran-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / DMAP / CH₂Cl₂ / 1 h / -78 °C

2: 89 percent / Pd₂(DBA)3*CHCl₃; PPh₃ / CH₂Cl₂ / 1 h / 0 °C

3: 90 percent / aq. HF / acetonitrile / 8 h / 0 °C

4: 92 percent / Pd₂(DBA)3*CHCl₃; PPh₃ / CH₂Cl₂ / 6 h / 0 °C

5: 90 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; hydrogen fluoride; triphenylphosphine; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja039400n