(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

Base Information

Chemical Name:(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde
CAS No.:128329-33-9
Molecular Formula:C₃₀H₃₄O₄
Molecular Weight:458.598
Hs Code.:

Synonyms:(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

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Chemical Property of (4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

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Technology Process of (4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

There total 15 articles about (4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde 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:

: [(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-methanol

: 128329-33-9
(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja00169a041

Reference yield:

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

: 128329-33-9
(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 13 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

12: lithium aluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

13: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; potassium hexamethylsilazane; dimethyl sulfoxide; 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

: 128329-33-9
(4S,5R,6R)-2,2,5-Trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 10 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

9: lithium aluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

10: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

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