Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester
CAS No.:862670-52-8
Molecular Formula:C₂₆H₄₀O₆Si
Molecular Weight:476.686
Hs Code.:

Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

There total 19 articles about Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-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:

: Benzoic acid (2S,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-formyl-tetrahydro-furan-3-yl ester

: 1779-49-3
Methyltriphenylphosphonium bromide

: 862670-52-8
Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 23 ℃; for 1h;

Benzoic acid (2S,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-formyl-tetrahydro-furan-3-yl ester; In tetrahydrofuran; at -78 - 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

: 679812-24-9
(2R,3R)-2-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-pentanal

: 862670-52-8
Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 71 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.67 h / -78 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

2.2: 98 percent / Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

3.1: 70 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

4.1: 83 percent / CSA / methanol / 2 h / 21 °C

5.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 21 h / 0 - 24 °C

6.1: 86 percent / DDQ / CH₂Cl₂; H₂O / 3.5 h / 25 °C / pH 7

7.1: 90 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2 h / 24 °C

8.1: 88 percent / TBAF / dimethylformamide; acetic acid / 3.3 h / 23 °C

9.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

9.2: Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

10.1: NHMDS / tetrahydrofuran / 1 h / 23 °C

10.2: tetrahydrofuran / 1 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; oxalyl dichloride; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 2.1: Swern oxidation / 9.1: Swern oxidation / 10.1: Wittig reaction;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

: (R)-4-[(R)-3-(4-Methoxy-benzyloxy)-1-methyl-propyl]-2-phenyl-[1,3]dioxolane

: 862670-52-8
Benzoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 74 percent / DIBALH / benzene / 1.5 h / 0 °C

2.1: 97 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 71 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.67 h / -78 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 98 percent / Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

5.1: 70 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

6.1: 83 percent / CSA / methanol / 2 h / 21 °C

7.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 21 h / 0 - 24 °C

8.1: 86 percent / DDQ / CH₂Cl₂; H₂O / 3.5 h / 25 °C / pH 7

9.1: 90 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2 h / 24 °C

10.1: 88 percent / TBAF / dimethylformamide; acetic acid / 3.3 h / 23 °C

11.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

11.2: Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

12.1: NHMDS / tetrahydrofuran / 1 h / 23 °C

12.2: tetrahydrofuran / 1 h / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; oxalyl dichloride; dimethyl pimelimidate dihydrochloride; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; benzene; 2.1: Dess-Martin oxidation / 4.1: Swern oxidation / 11.1: Swern oxidation / 12.1: Wittig reaction;
DOI:10.1016/j.tetlet.2005.05.062