2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

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Chemical Name:2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester
CAS No.:475641-75-9
Molecular Formula:C₂₂H₃₀O₆
Molecular Weight:390.477
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

There total 22 articles about 2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl 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: 80.0%

: 3282-30-2
pivaloyl chloride

: 475641-74-8
(2S,3R)-2-((2R,4S,5R)-2-Phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-ene-1,3-diol

: 475641-75-9
2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

Guidance literature:: With pyridine; at 25 ℃; for 2.5h;
DOI:10.1055/s-2002-33527

Reference yield:

: 83938-00-5
((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate

: 475641-75-9
2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: Amberlyst 15 / methanol / 24 h / Heating

2.1: Amberlyst 15 / CHCl₃ / 22.5 h

3.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

4.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

5.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

6.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

7.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C

7.2: 79 percent / tetrahydrofuran / 1 h / -78 °C

8.1: 100 percent / TBAF / tetrahydrofuran / 22 °C

9.1: aq. NaIO₄ / dioxane / 22 °C

10.1: NaBH₄ / methanol / 0 °C

11.1: 95 percent / benzene / Heating

12.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 25 °C

13.1: 92 percent / aq. H₂O₂ / ethyl acetate / 6 h / 20 °C

14.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 18 h / 25 °C

15.1: 100 percent / DIBALH / CH₂Cl₂ / 0.13 h / -78 °C

16.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - -20 °C

17.1: NaHMDS / tetrahydrofuran / 1 h / 25 °C

17.2: 83 percent / tetrahydrofuran / 0.1 h / -78 °C

18.1: 100 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

19.1: 80 percent / pyridine / 2.5 h / 25 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; ethyl acetate; benzene; 16.1: Swern oxidation / 17.2: Wittig reaction;
DOI:10.1055/s-2002-33527

Reference yield:

: 88180-36-3
2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

: 475641-75-9
2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: Amberlyst 15 / CHCl₃ / 22.5 h

2.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

4.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

5.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

6.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C

6.2: 79 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 100 percent / TBAF / tetrahydrofuran / 22 °C

8.1: aq. NaIO₄ / dioxane / 22 °C

9.1: NaBH₄ / methanol / 0 °C

10.1: 95 percent / benzene / Heating

11.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 25 °C

12.1: 92 percent / aq. H₂O₂ / ethyl acetate / 6 h / 20 °C

13.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 18 h / 25 °C

14.1: 100 percent / DIBALH / CH₂Cl₂ / 0.13 h / -78 °C

15.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - -20 °C

16.1: NaHMDS / tetrahydrofuran / 1 h / 25 °C

16.2: 83 percent / tetrahydrofuran / 0.1 h / -78 °C

17.1: 100 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

18.1: 80 percent / pyridine / 2.5 h / 25 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; ethyl acetate; benzene; 15.1: Swern oxidation / 16.2: Wittig reaction;
DOI:10.1055/s-2002-33527