(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dimethyl-propionyloxy)-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-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:198200-58-7
Molecular Formula:C₂₆H₄₂O₈Si
Molecular Weight:510.7
Hs Code.:

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

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

There total 15 articles about (2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dimethyl-propionyloxy)-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: 96.0%

: 3282-30-2
pivaloyl chloride

: 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

: 198200-58-7
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With dmap; In pyridine; at 40 ℃; for 18h;
DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

: 79-22-1
methyl chloroformate

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

: 198200-58-7
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h; Yield given;
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

: 198200-58-7
(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / 4 Angstroem molecular sieves, pyridine / 3 h / 0 °C

2: 89 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

3: 41 percent / diborane*THF / tetrahydrofuran / 4 h / Ambient temperature

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

5: Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; B₂H₆-THF; 4 A molecular sieve; sulfuric acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(97)00149-3