(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:198200-57-6
Molecular Formula:C₂₁H₃₄O₇Si
Molecular Weight:426.582
Hs Code.:

Synonyms:(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 9 articles about (2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl 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: 71.0%

: 198200-54-3
(2R,3S,4R,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 198200-57-6
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With sodium methylate; In methanol; at 40 ℃; for 5h;
DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

: 198200-41-8
(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

: 198200-57-6
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / 4 Angstroem molecular sieves, pyridine / 0.5 h / -30 °C

2: 97 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

3: 54 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 2.5 h / 65 °C

4: 84 percent / chromium trioxide, conc. H₂SO₄ / acetone; H₂O / 0 °C

5: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 71 percent / NaOMe / methanol / 5 h / 40 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; sulfuric acid; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

: 198200-37-2
methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

: 198200-57-6
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / pyridine / 2 h / Ambient temperature

2: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

3: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

4: 89 percent / 4 Angstroem molecular sieves, pyridine / 0.5 h / -30 °C

5: 97 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

6: 54 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 2.5 h / 65 °C

7: 84 percent / chromium trioxide, conc. H₂SO₄ / acetone; H₂O / 0 °C

8: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

9: 71 percent / NaOMe / methanol / 5 h / 40 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; sulfuric acid; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(97)00149-3