(1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane

Base Information

• Chemical Name: (1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane
• CAS No.: 186525-52-0
• Molecular Formula: C₂₂H₂₉NO₇
• Molecular Weight: 419.475

Synonyms:(1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane

Chemical Property of (1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane

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Technology Process of (1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane

There total 1 articles about (1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane 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:

(R)-1-phenyl-ethyl-amine (3886-69-9) + (4S,5S)-4-Acetoxy-5-((S)-2-methoxycarbonyl-oxiranyl)-3a,4,5,6-tetrahydro-3H-cyclopentapyrazole-6a-carboxylic acid methyl ester → (1R,3S,4S,5S,1'S)-(+)-4-acetyloxy-3-(1'-hydroxy-1'-methoxycarbonyl-1'-<(R)-α-methylbenzylaminomethyl>methyl)-1-methoxycarbonylbicyclo<3.1.0>hexane (172214-85-6) + (1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane (186525-52-0)

Guidance literature:

With benzophenone; Multistep reaction; 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) DMF, 60 deg C, 24 h;

DOI:10.1016/S0957-4166(96)00454-5

Reference yield: 80.0%

(1S,3S,4S,5R,1'S)-(+)-4-acetyloxy-3-[1'-hydroxy-1'-methoxycarbonyl-1'-((R)-α-methylbenzylaminomethyl)methyl]-1-methoxycarbonylbicyclo[3.1.0]hexane (186525-52-0) → (1S,3S,4S,5R,1'S)-(-)-3-[1'-carboxy-1'-hydroxy-1'-((R)-α-methylbenzylaminomethyl)methyl]-4-hydroxybicyclo[3.1.0]hexane-1-carboxylic acid (186525-74-6)

Guidance literature:

With sodium hydroxide; In methanol; at 60 ℃; for 1h;

DOI:10.1016/S0957-4166(96)00454-5

upstream raw materials:

(R)-1-phenyl-ethyl-amine

Downstream raw materials:

(1S,3S,4S,5R,1'S)-(-)-3-[1'-carboxy-1'-hydroxy-1'-((R)-α-methylbenzylaminomethyl)methyl]-4-hydroxybicyclo[3.1.0]hexane-1-carboxylic acid

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