(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

Base Information

Chemical Name:(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane
CAS No.:158584-97-5
Molecular Formula:C₂₂H₃₂N₂O₅
Molecular Weight:404.506
Hs Code.:

Synonyms:(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

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Chemical Property of (3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

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Technology Process of (3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

There total 20 articles about (3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane 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:

: 158584-94-2
(4R,5R)-3-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethyl-5-<3''-hydroxypropyl>-2,2-dimethyl-1,3-oxazolidine

: 158584-97-5
(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

2: 1.) (CF₃SO₂)2O, 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, 20 deg C, 20 h

3: H₂ / 10percent Pd/C / ethanol / 24 h

4: Et₃N / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/0957-4166(96)00381-3

Reference yield:

: 171564-51-5
(4R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-4-methanesulfonyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 158584-97-5
(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 25 ℃; Yield given;
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

: 158584-97-5
(3R,4R)-N-benzyloxycarbonyl-3,4-<3'-N-tert-butoxycarbonyl-2',2'-dimethyl-1',3'-oxazolidinyl> azepane

Guidance literature:: Multi-step reaction with 9 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

8: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

9: t-BuOK / tetrahydrofuran / 0.17 h / 25 °C

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