(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

Base Information

Chemical Name:(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester
CAS No.:99458-23-8
Molecular Formula:C₂₈H₃₅NO₅
Molecular Weight:465.59
Hs Code.:

Synonyms:(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

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Chemical Property of (2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

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Technology Process of (2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

There total 7 articles about (2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl 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%

: 1196-00-5
(-)-isopinocampheol

: 99458-20-5
(2R,3S)-N-benzoyl-O-(methoxymethyl)-3-phenylisoserine

: 99458-23-8
(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 1.) 0deg C, 5 min, 2.) 20 deg C, 15 h;
DOI:10.1021/jo00351a008

Reference yield:

: 99458-15-8
Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate

: 99458-23-8
(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h

2: 1.) H₂ / 1.) 10percent Pd/C / 1.) CH₃OH, 15 h, 2.) CH₃OH, RT, 72 h

3: 82 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 h

4: 100 percent / potassium carbonate / methanol; H₂O / 15 h

5: 70 percent / 4-(dimethylamino)pyridine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0deg C, 5 min, 2.) 20 deg C, 15 h

With dmap; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; water;
DOI:10.1021/jo00351a008

Reference yield:

: 99528-63-9
(2S,3R)-2,3-epoxy-3-phenylpropan-1-ol

: 99458-23-8
(2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) sodium bicarbonate, sodium periodate, ruthenium trichloride trihydrate / 1.) CCl₄, acetonitrile, water, 20 deg C, 44 h, 2.) Et₂O

2: 90 percent / azidotrimethylsilane, zinc chloride / 48 h / 68 °C

3: 94 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h

4: 1.) H₂ / 1.) 10percent Pd/C / 1.) CH₃OH, 15 h, 2.) CH₃OH, RT, 72 h

5: 82 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 h

6: 100 percent / potassium carbonate / methanol; H₂O / 15 h

7: 70 percent / 4-(dimethylamino)pyridine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0deg C, 5 min, 2.) 20 deg C, 15 h

With dmap; ruthenium trichloride; sodium periodate; trimethylsilylazide; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; palladium on activated charcoal; In methanol; dichloromethane; water;
DOI:10.1021/jo00351a008