(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester
CAS No.:321378-07-8
Molecular Formula:C₂₉H₃₈N₂O₇
Molecular Weight:526.63
Hs Code.:

Synonyms:(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

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Chemical Property of (4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

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Technology Process of (4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

There total 6 articles about (4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl 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: 70.0%

: 77-76-9
2,2-dimethoxy-propane

: 321377-99-5
(2S,3R)-2-(4-Benzyloxy-benzoylamino)-6-tert-butoxycarbonylamino-3-hydroxy-hexanoic acid methyl ester

: 321378-07-8
(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 25 ℃;
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

: 321378-07-8
(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 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

With CODRu(2-methylallyl)2; hydrogen; toluene-4-sulfonic acid; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); palladium on activated charcoal; In methanol; 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

: 321378-07-8
(4S,5R)-3-(4-Benzyloxy-benzoyl)-5-(3-tert-butoxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

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