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

Base Information

Chemical Name:(-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate
CAS No.:427882-52-8
Molecular Formula:C₂₂H₂₅NO₅
Molecular Weight:383.444
Hs Code.:

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

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

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

There total 9 articles about (-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-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: 68.0%

: 427882-51-7
(-)-methyl (1R,4S,5S,7R)-3-benzyl-4exo-(O-benzylhydroxymethyl)-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

: 427882-52-8
(-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield: 19.0%

: 427882-51-7
(-)-methyl (1R,4S,5S,7R)-3-benzyl-4exo-(O-benzylhydroxymethyl)-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate

: (-)-(1S,2S,5S,6S)-3-benzyl-2exo-(benzyloxymethyl)-6exo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane

: 427882-52-8
(-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; for 0.25h; Heating;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield:

: 19525-87-2
O-methyl O-benzyl-L-serinate hydrochloride

: 427882-52-8
(-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

2: 98 percent / LiAlH₄ / tetrahydrofuran

3: 70 percent / PyBrOP; DIPEA / CH₂Cl₂

4: 2.03 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

5: 57 percent / H₂SO₄; SiO₂ / benzene / 0.33 h / Heating

6: 56 percent / BH₃*DMS / tetrahydrofuran / 0.25 h / Heating

With lithium aluminium tetrahydride; dimethylsulfide borane complex; sulfuric acid; silica gel; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V