(1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

Base Information

• Chemical Name: (1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one
• CAS No.: 1424361-00-1
• Molecular Formula: C₂₀H₂₅NO₅S
• Molecular Weight: 391.488
• Mol file: 1424361-00-1.mol

Synonyms:(1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

Chemical Property of (1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

There total 1 articles about (1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-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: 73.0%

para-methanesulfonylbenzaldehyde (5398-77-6) + (1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one (500137-55-3) → (1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one (1424361-00-1)

Guidance literature:

(1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one; With n-butyllithium; lithium perchlorate; diisopropylamine; In tetrahydrofuran; at -78 - -40 ℃; for 1.16667h; Inert atmosphere;

para-methanesulfonylbenzaldehyde; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/cjoc.201201093

Reference yield: 91.0%

(1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one (1424361-00-1) → (2S,3R)-3-[p-(methylsulfonyl)phenyl]-3-hydroxy-2-aminopropanoic acid

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 3.5h; Sealed tube; Inert atmosphere;

DOI:10.1002/cjoc.201201093

Reference yield:

(1S,2R,5S,8R,1’R)-5-(1’-hydroxy(p-methylsulfonyl)benzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one (1424361-00-1) → thiamphenicol (15318-45-3,90-91-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / water / 3.5 h / 80 °C / Sealed tube; Inert atmosphere

2: thionyl chloride / 40 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 60 °C / Inert atmosphere

4: triethylamine / methanol / 8 h / 30 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; triethylamine; In methanol; water;

DOI:10.1002/cjoc.201201093

upstream raw materials:

para-methanesulfonylbenzaldehyde

(1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one

Downstream raw materials:

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

thiamphenicol

(2S,3R)-methyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate