(2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

Base Information

Chemical Name:(2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one
CAS No.:118628-36-7
Molecular Formula:C₁₅H₁₇NO₄
Molecular Weight:275.304
Hs Code.:

Synonyms:(2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

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Chemical Property of (2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

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Technology Process of (2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

There total 17 articles about (2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one 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:

: 62772-19-4,62772-20-7,118628-36-7,118628-37-8
(R)-3,3-Dimethyl-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

: 118628-36-7
(2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform-d1; at 55 ℃; for 8h; Yield given;
DOI:10.1021/jo00265a054

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 118628-36-7
(2R,5R)-3,3-dimethyl-2-<(benzyloxy)carbonyl>-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 5 steps

1: 25 percent / silver nitrite / tetrahydrofuran; toluene / 1.) -25 deg C, 1 h, 2.) 0 deg C, 1 h

2: 1.) potassium tert butoxide / 1.) tert-butyl alcohol, THF, 0 deg C, 15 min, 2.) 3 h

3: 1.) methanesulfonyl chloride, diisopropylethylamine, dimethylaminopyridine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dimethylaminopyridine / 1.) CH₂Cl₂, -78 deg C to RT, 19 h, 2.) 1 h

4: 1.) tetrabutylammonium fluoride, 2.) ozone / 1.) -55 deg C, 10 min, THF, 2.) -78 deg C, THF/CH₂Cl₂

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / CDCl₃ / 8 h / 55 °C

With dmap; silver(I) nitrite; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dmap; In tetrahydrofuran; chloroform-d1; toluene;
DOI:10.1021/jo00265a054

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 62772-19-4,62772-20-7,118628-36-7,118628-37-8
(R)-3,3-Dimethyl-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 25 percent / silver nitrite / tetrahydrofuran; toluene / 1.) -25 deg C, 1 h, 2.) 0 deg C, 1 h

2: 1.) potassium tert butoxide / 1.) tert-butyl alcohol, THF, 0 deg C, 15 min, 2.) 3 h

3: 1.) methanesulfonyl chloride, diisopropylethylamine, dimethylaminopyridine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dimethylaminopyridine / 1.) CH₂Cl₂, -78 deg C to RT, 19 h, 2.) 1 h

4: 1.) tetrabutylammonium fluoride, 2.) ozone / 1.) -55 deg C, 10 min, THF, 2.) -78 deg C, THF/CH₂Cl₂

With dmap; silver(I) nitrite; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dmap; In tetrahydrofuran; toluene;
DOI:10.1021/jo00265a054