(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

Base Information

Chemical Name:(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate
CAS No.:427882-61-9
Molecular Formula:C₁₅H₁₅NO₅
Molecular Weight:289.288
Hs Code.:

Synonyms:(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

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Chemical Property of (-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

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Technology Process of (-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

There total 5 articles about (-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate 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: 28.0%

: 427882-50-6
methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

: 427882-61-9
(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

: (R)-((R)-4-Benzyl-6-hydroxy-5-methylene-3-oxo-morpholin-2-yl)-hydroxy-acetic acid methyl ester

Guidance literature:: With sulfuric acid; silica gel; In benzene; for 0.333333h; Heating;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield:

: 98-88-4
benzoyl chloride

: 427882-61-9
(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 5 percent / Et₃N / tetrahydrofuran / 15 h / 20 °C

2: 98 percent / LiAlH₄ / tetrahydrofuran

3: 70 percent / PyBrOP; DIPEA / CH₂Cl₂

4: 72 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

5: 28 percent / H₂SO₄; SiO₂ / benzene / 0.33 h / Heating

With lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; silica gel; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; dichloromethane; benzene; 4: Swern oxidation;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield:

: 170956-48-6
(2R)-(+)-2-(N-benzylamino)-3-benzyloxy-1-propanol

: 427882-61-9
(-)-methyl (1R,5S,7R)-3-benzyl-4-methylene-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / PyBrOP; DIPEA / CH₂Cl₂

2: 72 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

3: 28 percent / H₂SO₄; SiO₂ / benzene / 0.33 h / Heating

With oxalyl dichloride; sulfuric acid; silica gel; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; benzene; 2: Swern oxidation;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V