Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
CAS No.:381727-54-4
Molecular Formula:C₂₀H₃₂O₅Si
Molecular Weight:380.557
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 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:

: 98-88-4
benzoyl chloride

: 99371-23-0
Methyl-3-O-<(tert-butyl)(dimethyl)silyl>-2,6-didesoxy-α-D-arabino-hexopyranosid

: 381727-54-4
Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1002/anie.200604031

Reference yield:

: 13322-79-7
(2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol

: 381727-54-4
Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole; DMAP / dimethylformamide / 6 h / 20 °C

2: N,N,N',N'-tetramethylethylenediamine / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; N,N,N,N,-tetramethylethylenediamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200604031

Reference yield:

: 18546-25-3
6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

: 381727-54-4
Benzoic acid (2R,3R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaBr; NaHCO₃ / dimethylformamide / 12 h / 65 °C

2: 13.0 g / Bu₃SnH; AIBN / toluene / 1.5 h / 110 °C

3: 80 percent / LiBr; Dowex(R) 50Wx₄ / acetonitrile / 3 h / 20 °C

4: 95 percent / NaOMe; MeOH / 2 h / 20 °C

5: imidazole; DMAP / dimethylformamide / 6 h / 20 °C

6: N,N,N',N'-tetramethylethylenediamine / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; methanol; dmap; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; Dowex(R) 50WX₄; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; sodium bromide; lithium bromide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/anie.200604031