(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

Base Information

Chemical Name:(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester
CAS No.:307494-03-7
Molecular Formula:C₂₆H₃₂N₄O₅Si
Molecular Weight:508.649
Hs Code.:

Synonyms:(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

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Chemical Property of (2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

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Technology Process of (2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

There total 6 articles about (2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl 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: 89.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 307494-02-6
(2S,3S)-2-Azido-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-pentanoic acid benzyl ester

: 307494-03-7
(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at 5 ℃; for 12h;
DOI:10.1016/S0040-4039(00)01204-1

Reference yield:

: 2436-29-5
3-(N-phthaloyl)propionaldehyde

: 307494-03-7
(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaOH; triethylamine / CH₂Cl₂; H₂O / 20 °C

2: 82 percent / AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 5 °C

3: pyridine; CH₂Cl₂ / 72 h / 5 °C

4: NaN₃ / dimethylformamide / 12 h / 60 °C

5: 89 percent / 2,4,6-collidine / CH₂Cl₂ / 12 h / 5 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; AD-mix-α; sodium azide; methanesulfonamide; triethylamine; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Condensation / 2: Sharpless asymmetric dihydroxylation / 3: Condensation / 4: Substitution / 5: silylation;
DOI:10.1016/S0040-4039(00)01204-1

Reference yield:

: 78385-36-1
benzyloxycarbonylmethyltriphenylphosphonium bromide

: 307494-03-7
(2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaOH; triethylamine / CH₂Cl₂; H₂O / 20 °C

2: 82 percent / AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 5 °C

3: pyridine; CH₂Cl₂ / 72 h / 5 °C

4: NaN₃ / dimethylformamide / 12 h / 60 °C

5: 89 percent / 2,4,6-collidine / CH₂Cl₂ / 12 h / 5 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; AD-mix-α; sodium azide; methanesulfonamide; triethylamine; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Condensation / 2: Sharpless asymmetric dihydroxylation / 3: Condensation / 4: Substitution / 5: silylation;
DOI:10.1016/S0040-4039(00)01204-1