methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

Base Information

Chemical Name:methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate
CAS No.:460054-09-5
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

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Chemical Property of methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

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Technology Process of methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

There total 9 articles about methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate 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: 79.0%

: 460054-07-3
methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-(2-oxopropyl)-3-vinylpiperidine-1-carboxylate

: 460054-09-5
methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

Guidance literature:: With sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; at 20 ℃; for 8h;
DOI:10.1021/jo025929b

Reference yield:

: (2S,3S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-carboxymethyl-3-vinyl-piperidine-1-carboxylic acid methyl ester

: 460054-09-5
methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 741 mg / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2.1: 96 percent / tetrahydrofuran / 1 h / 20 °C

3.1: 79 percent / OsO₄; sodium metaperiodate / dioxane; H₂O / 8 h / 20 °C

With sodium periodate; osmium(VIII) oxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/jo025929b

Reference yield:

: 442202-22-4
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

: 460054-09-5
methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiOH*H₂O / methanol; H₂O / 2 h / Heating

2.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

3.1: diethyl ether / 15 h / 20 °C

4.1: 2.4 g / silver benzoate; Et₃N / 9 h / 20 °C

5.1: LiOH*H₂O / methanol; H₂O / 1 h / Heating

6.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 741 mg / triethylamine / CH₂Cl₂ / 16 h / 20 °C

7.1: 96 percent / tetrahydrofuran / 1 h / 20 °C

8.1: 79 percent / OsO₄; sodium metaperiodate / dioxane; H₂O / 8 h / 20 °C

With lithium hydroxide; sodium periodate; osmium(VIII) oxide; silver benzoate; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo025929b