(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one

Base Information

• Chemical Name: (1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one
• CAS No.: 903517-94-2
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.278

Synonyms:(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one

Chemical Property of (1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one

Chemical Property:

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Technology Process of (1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one

There total 1 articles about (1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-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: 84.0%

(1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester (220623-03-0) → (1S,1aS,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carbaldehyde + (1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.02,4]nonan-5-one (903517-94-2)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo060210f

Reference yield: 75.0%

(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.02,4]nonan-5-one (903517-94-2) → (1S,2R,3S,4S,7R)-6-aza-3-(chloromethyl)-8-oxa-7-phenyltricyclo[4.3.0.02,4]nonan-5-one

Guidance literature:

With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1021/jo060210f

Reference yield: 70.0%

(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.02,4]nonan-5-one (903517-94-2) + methanesulfonyl chloride (124-63-0) → ((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)methyl methylsulfonate (903517-98-6)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/jo060210f

upstream raw materials:

(1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester

Downstream raw materials:

((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)methyl methylsulfonate

2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile

[(1S,2S,5R,6R)-6-(2-aminoethyl)-3-aza-3-benzylbicyclo[3.1.0]hex-2-yl]methanol

[2-((1S,2S,5R,6R)-3-Benzyl-2-hydroxymethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-ethyl]-carbamic acid tert-butyl ester

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