(1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

Base Information

• Chemical Name: (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one
• CAS No.: 423157-99-7
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.32

Synonyms:(1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

Chemical Property of (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

Chemical Property:

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Technology Process of (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

There total 5 articles about (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-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: 70.0%

N-methylhydroxyamine hydrochloride (4229-44-1) + (+)-(3R,4R)-3-benzyloxy-1-(2-propenyl)-4-oxoazetidine-2-carbaldehyde (253599-41-6) → (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (423157-99-7)

Guidance literature:

With triethylamine; In toluene; for 0.5h; Heating;

DOI:10.1002/ejoc.200400792

Reference yield:

Benzyloxyacetyl chloride (19810-31-2) → (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (423157-99-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

2: p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

3: 773 mg / sodium periodate / CH₂Cl₂

4: 70 percent / NEt₃ / toluene / 0.5 h / Heating

With sodium periodate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 1: Staudinger reaction;

DOI:10.1002/ejoc.200400792

Reference yield:

(+)-cis-1-allyl-3-(R)-benzyloxy-4-(S)-[1-(S),2-dihydroxyethyl]-azetidin-2-one (253599-40-5) → (1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (423157-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 773 mg / sodium periodate / CH₂Cl₂

2: 70 percent / NEt₃ / toluene / 0.5 h / Heating

With sodium periodate; triethylamine; In dichloromethane; toluene;

DOI:10.1002/ejoc.200400792

upstream raw materials:

N-methylhydroxyamine hydrochloride

(+)-(3R,4R)-3-benzyloxy-1-(2-propenyl)-4-oxoazetidine-2-carbaldehyde

Benzyloxyacetyl chloride

(+)-cis-1-allyl-3-(R)-benzyloxy-4-(S)-[1-(S),2-dihydroxyethyl]-azetidin-2-one

Downstream raw materials:

1-[(1S,2S,5R)-2-((R)-1-Benzyloxy-2-hydroxy-ethyl)-7-methyl-6-oxa-3,7-diaza-bicyclo[3.2.1]oct-3-yl]-propenone

(R)-((1S,2S,5R)-3-Acryloyl-7-methyl-6-oxa-3,7-diaza-bicyclo[3.2.1]oct-2-yl)-benzyloxy-acetaldehyde

(R)-2-Benzyloxy-2-((1S,2S,5R)-7-methyl-6-oxa-3,7-diaza-bicyclo[3.2.1]oct-2-yl)-ethanol

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