(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

Base Information

Chemical Name:(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester
CAS No.:422570-14-7
Molecular Formula:C₂₀H₂₅NO₅
Molecular Weight:359.422
Hs Code.:

Synonyms:(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

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Chemical Property of (1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

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Technology Process of (1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

There total 5 articles about (1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-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: 98.8%

: 23963-16-8
(1S,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 422570-14-7
(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 18h;
DOI:10.1021/jo011139a

Reference yield:

: 10334-26-6
(R)-camphorquinone

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 422570-14-7
(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

: 500137-54-2
(1S,2R,4R)-benzyloxycarbonylaminoacetic acid 4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

Guidance literature:: (R)-camphorquinone; With sodium tetrahydroborate; In methanol; diethyl ether; for 0.5h; cooling;

N-(Benzyloxycarbonyl)glycine; With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 18h; Title compound not separated from byproducts;
DOI:10.1021/jo052435g

Reference yield:

: 464-49-3,68546-28-1
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

: 422570-14-7
(1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99.6 percent / SeO₂ / acetic anhydride / 17 h / Heating

2.1: 78 percent / p-toluenesulfonic acid monohydrate / benzene / 24 h / Heating

3.1: NaBH₄ / diethyl ether; methanol / 3.5 h / 0 °C

3.2: 94 percent / conc. H₂SO₄ / H₂O / ice-cold

4.1: 98.8 percent / 4-N,N-(dimethylamino)pyridine; dicyclohexylcarbodiimide / tetrahydrofuran / 18 h / 0 - 20 °C

With dmap; sodium tetrahydroborate; selenium(IV) oxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; acetic anhydride; benzene;
DOI:10.1021/jo011139a