2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester
CAS No.:128329-31-7
Molecular Formula:C₃₅H₄₄O₅
Molecular Weight:544.731
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

There total 28 articles about 2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl 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:

: 128329-22-6
(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol

: 128329-31-7
2,2-Dimethyl-propionic acid (4R,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / triethylamine, DMAP / CH₂Cl₂ / 6 h

2: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) n-Bu₄NF, 2.) sodium methoxide / 1.) THF, RT, 2.) 0.5 h

4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) RT, overnight

5: ethyl((dimethylamino)propyl)carbodiimide hydrochloride (EDAC*HCl), DMAP / CH₂Cl₂ / 0.5 h / 0 °C

6: 30percent hydrogen peroxide / CH₂Cl₂ / 0.5 h / 0 °C

7: 97 percent / CuI, LiBr / diethyl ether / 1 h / -20 °C

8: 31 percent / KHMDS, MoOPH / tetrahydrofuran; toluene / -78 - -30 °C

9: 93 percent / lithium aluminum hydride / tetrahydrofuran / 4 h / Ambient temperature

10: 88 percent / pyridine / 1.) 0 deg C, 1 h, 2.) RT, 1 h

11: camphorsulfonic acid / various solvent(s) / 0.03 h

With pyridine; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00169a041

Reference yield:

: 128329-22-6
(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol

: 128329-31-7
2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / triethylamine, DMAP / CH₂Cl₂ / 6 h

2: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) n-Bu₄NF, 2.) sodium methoxide / 1.) THF, RT, 2.) 0.5 h

4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) RT, overnight

5: ethyl((dimethylamino)propyl)carbodiimide hydrochloride (EDAC*HCl), DMAP / CH₂Cl₂ / 0.5 h / 0 °C

6: 30percent hydrogen peroxide / CH₂Cl₂ / 0.5 h / 0 °C

7: 97 percent / CuI, LiBr / diethyl ether / 1 h / -20 °C

8: 53 percent / KHMDS, MoOPH / tetrahydrofuran; toluene / -78 - -30 °C

9: lithium aluminum hydride / tetrahydrofuran / 4 h / Ambient temperature

10: pyridine / 1.) 0 deg C, 1 h, 2.) RT, 1 h

11: camphorsulfonic acid / various solvent(s) / 0.03 h

With pyridine; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00169a041

Reference yield:

: 128329-24-8
(2R,3R)-1,2-epoxy-3-methyl-4<(triphenylsilyl)oxy>butane

: 128329-31-7
2,2-Dimethyl-propionic acid (4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) RT, overnight

2: ethyl((dimethylamino)propyl)carbodiimide hydrochloride (EDAC*HCl), DMAP / CH₂Cl₂ / 0.5 h / 0 °C

3: 30percent hydrogen peroxide / CH₂Cl₂ / 0.5 h / 0 °C

4: 97 percent / CuI, LiBr / diethyl ether / 1 h / -20 °C

5: 53 percent / KHMDS, MoOPH / tetrahydrofuran; toluene / -78 - -30 °C

6: lithium aluminum hydride / tetrahydrofuran / 4 h / Ambient temperature

7: pyridine / 1.) 0 deg C, 1 h, 2.) RT, 1 h

8: camphorsulfonic acid / various solvent(s) / 0.03 h

With pyridine; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00169a041