1,3-Dioxolane-4-carboxaldehyde, 5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl) -2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)-

Base Information

Chemical Name:1,3-Dioxolane-4-carboxaldehyde, 5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl) -2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)-
CAS No.:583039-99-0
Molecular Formula:C24H37NO5Si
Molecular Weight:447.647
Hs Code.:

1,3-Dioxolane-4-carboxaldehyde,
5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl)
-2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)-

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Chemical Property of 1,3-Dioxolane-4-carboxaldehyde, 5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl) -2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)-

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Technology Process of 1,3-Dioxolane-4-carboxaldehyde, 5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl) -2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)-

There total 7 articles about 1,3-Dioxolane-4-carboxaldehyde, 5-[(S)-[[(1,1-dimethylethyl)dimethylsilyl]oxy][(2R)-5-oxo-1-(phenylmethyl) -2-pyrrolidinyl]methyl]-2,2-dimethyl-, (4R,5R)- 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: 98.0%

: 583040-19-1
(R)-1-Benzyl-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-pyrrolidin-2-one

: 583039-99-0
(1'S,2''R,4R,5S)-5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -80 - 25 ℃; for 2.5h;
DOI:10.1021/jo0344539

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 583039-99-0
(1'S,2''R,4R,5S)-5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / SnCl₄ / diethyl ether; CH₂Cl₂ / 5 h / -80 °C

2: 92 percent / NaBH₄; NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Heating

4: 98 percent / ceric ammonium nitrate / acetonitrile / 2 h / Heating

5: 70 percent / KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

6: 80 percent / H₂; NaOAc / palladium hydroxyde / methanol / 24 h / 20 °C

7: 98 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -80 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; hydrogen; sodium acetate; tin(IV) chloride; potassium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 7: Swern oxidation;
DOI:10.1021/jo0344539

Reference yield:

: 141293-20-1
(1'S,2R,4''S,5''S)-2-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 583039-99-0
(1'S,2''R,4R,5S)-5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / NaBH₄; NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Heating

3: 98 percent / ceric ammonium nitrate / acetonitrile / 2 h / Heating

4: 70 percent / KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

5: 80 percent / H₂; NaOAc / palladium hydroxyde / methanol / 24 h / 20 °C

6: 98 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -80 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; hydrogen; sodium acetate; potassium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 6: Swern oxidation;
DOI:10.1021/jo0344539