(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester
CAS No.:321378-13-6
Molecular Formula:C₂₈H₃₆N₂O₅
Molecular Weight:480.604
Hs Code.:

Synonyms:(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

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Chemical Property of (3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

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Technology Process of (3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

There total 9 articles about (3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-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:

: 321378-11-4
Methanesulfonic acid (4R,5R)-3-(4-benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidin-4-ylmethyl ester

: 321378-13-6
(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;
DOI:10.1002/1099-0690(200012)2000:23<3903::AID-EJOC3903>3.0.CO;2-Q

Reference yield:

: 1486-50-6
4-(benzyloxy)benzoic acid chloride

: 321378-13-6
(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂; p-toluenesulfonic acid / Pd/C / methanol / 750.06 Torr

1.2: 69 percent / triethylamine / CH₂Cl₂

2.1: 80 percent / (R)-MeO-BIPHEP; CODRu(2-methallyl)2; H₂ / CH₂Cl₂ / 96 h / 50 °C / 97507.8 Torr

3.1: 70 percent / p-toluenesulfonic acid / acetone / 25 °C

4.1: 89 percent / calcium chloride; sodium borohydride / tetrahydrofuran; ethanol

5.1: triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

6.1: potassium tert-butoxide / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; CODRu(2-methylallyl)2; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone;
DOI:10.1002/1099-0690(200012)2000:23<3903::AID-EJOC3903>3.0.CO;2-Q

Reference yield:

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 321378-13-6
(3aR,8aR)-3-(4-Benzyloxy-benzoyl)-2,2-dimethyl-octahydro-1-oxa-3,5-diaza-azulene-5-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 78 percent / carbonyl diimidazole / tetrahydrofuran / 18 h / 25 °C

2.1: sodium nitrite / acetic acid; H₂O / 1 h / 0 °C

3.1: H₂; p-toluenesulfonic acid / Pd/C / methanol / 750.06 Torr

3.2: 69 percent / triethylamine / CH₂Cl₂

4.1: 80 percent / (R)-MeO-BIPHEP; CODRu(2-methallyl)2; H₂ / CH₂Cl₂ / 96 h / 50 °C / 97507.8 Torr

5.1: 70 percent / p-toluenesulfonic acid / acetone / 25 °C

6.1: 89 percent / calcium chloride; sodium borohydride / tetrahydrofuran; ethanol

7.1: triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

8.1: potassium tert-butoxide / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; CODRu(2-methylallyl)2; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); triethylamine; 1,1'-carbonyldiimidazole; calcium chloride; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; acetone;
DOI:10.1002/1099-0690(200012)2000:23<3903::AID-EJOC3903>3.0.CO;2-Q