(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:158585-08-1
Molecular Formula:C₂₂H₃₄N₂O₆
Molecular Weight:422.522
Hs Code.:

Synonyms:(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 12 articles about (4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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: 96.0%

: 158584-96-4
(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 158585-08-1
(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 16h;
DOI:10.1021/ja00097a072

Reference yield:

: 158584-92-0
[(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

: 158585-08-1
(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: CSA / CH₂Cl₂ / 3 h / 25 °C

2: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, 20 h, 2.) MeOH, 25 deg C, 5 h

3: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

4: NaN₃ / dimethylformamide / 24 h / 25 °C

5: H₂ / 10percent Pd/C / tetrahydrofuran / 19 h / 25 °C

6: 3 N aq. NaOH / dioxane / 0.25 h / 0 °C

7: 96 percent / TBAF / tetrahydrofuran / 16 h / 25 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 171564-49-1
(4R,5R)-5-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 158585-08-1
(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, 20 h, 2.) MeOH, 25 deg C, 5 h

2: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: NaN₃ / dimethylformamide / 24 h / 25 °C

4: H₂ / 10percent Pd/C / tetrahydrofuran / 19 h / 25 °C

5: 3 N aq. NaOH / dioxane / 0.25 h / 0 °C

6: 96 percent / TBAF / tetrahydrofuran / 16 h / 25 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;