(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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:(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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.:862670-61-9
Molecular Formula:C₄₁H₇₂O₉Si₂
Molecular Weight:765.188
Hs Code.:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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

Synonyms:(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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 23 articles about (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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: 82.0%

: 862670-45-9
(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-ol

: 679812-27-2
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic acid

: 862670-61-9
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 862670-61-9
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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 3 steps

1: 98 percent / 2,6-lutidine / 1 h / 0 °C

2: 94 percent / LiOH; aq. H₂O₂ / tetrahydrofuran / 4 h / 24 °C

3: 82 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 23 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

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

: 862670-61-9
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2-methyl-heptanoic 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: 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

11.1: 86 percent / K₂CO₃ / methanol / 3.5 h / 23 °C

12.1: 82 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 23 °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; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; 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