(E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester

Base Information

• Chemical Name: (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester
• CAS No.: 164334-40-1
• Molecular Formula: C₂₆H₄₁N₂O₃P
• Molecular Weight: 460.597

Synonyms:(E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester

Chemical Property of (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester

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Technology Process of (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester

There total 3 articles about (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester 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:

tert-butyl cinnamate (14990-09-1) + (3aR,7aR)-2-crotyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide (150932-41-5) + methyl iodide (74-88-4) → (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester (164334-40-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo000388g

Reference yield:

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5) → (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester (164334-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N / benzene / 18 h / 20 °C

2: n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; hexane; benzene; 1: cyclocondensation / 2: Addition;

DOI:10.1021/jo000388g

Reference yield:

Lithium; (1Z,5E)-(3S,4R)-1-tert-butoxy-6-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-4-methyl-3-phenyl-hexa-1,5-dien-1-olate + methyl iodide (74-88-4) → (E)-(2S,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester + (E)-(2R,3S,4R)-6-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-2,4-dimethyl-3-phenyl-hex-5-enoic acid tert-butyl ester (164334-40-1)

Guidance literature:

In tetrahydrofuran; at -78 - -65 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)78330-4

upstream raw materials:

methyl iodide

tert-butyl cinnamate

(3aR,7aR)-2-crotyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

Downstream raw materials:

(2R,3S,4R)-5-Hydroxy-2,4-dimethyl-3-phenyl-pentanoic acid tert-butyl ester

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