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

Base Information

• Chemical Name: ((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)methyl methylsulfonate
• CAS No.: 903517-98-6
• Molecular Formula: C₁₅H₁₇NO₅S
• Molecular Weight: 323.37

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

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

Chemical Property:

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

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

(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

Reference yield:

(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,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:

Multi-step reaction with 2 steps

1: 84 percent / LiEt₃BH / tetrahydrofuran / 0.5 h / -78 °C

2: 70 percent / DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

With dmap; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo060210f

Reference yield: 84.0%

((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) + potassium cyanide (151-50-8) → 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)ethanenitrile (903518-00-3)

Guidance literature:

With tetra-n-butylammonium cyanide; In dichloromethane; water; at 20 ℃; for 72h;

DOI:10.1021/jo060210f

upstream raw materials:

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

methanesulfonyl chloride

(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:

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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