(2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester
• CAS No.: 586418-52-2
• Molecular Formula: C₂₈H₂₉NO₂
• Molecular Weight: 411.544
• Mol file: 586418-52-2.mol

Synonyms:(2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester

Chemical Property of (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester

There total 4 articles about (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-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: 71.0%

1-phenyl-2-propenyl acetate (7217-71-2) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl (S,E)-2-((diphenylmethylene)amino)-5-phenylpent-4-enoate + (2R,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-53-3) + (2S,3R)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (477741-39-2) + (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-52-2)

Guidance literature:

With potassium hydroxide; chiral phase transfer catalyst; chiral phosphine-type ligand; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In water; toluene; at 0 ℃; for 3.5h; Further byproducts given;

DOI:10.1021/jo034638f

Reference yield: 67.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + (E)-cinnamyl diethyl phosphate (85669-63-2) → (2R,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-53-3) + (2S,3R)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (477741-39-2) + (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-52-2)

Guidance literature:

With potassium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-4-(2-ethylsulfanylethoxy)-3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalene; In toluene; at 0 ℃; for 20h;

DOI:10.1002/anie.200250654

Reference yield: 3.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + (E)-cinnamyl diethyl phosphate (85669-63-2) → tert-butyl (S,E)-2-((diphenylmethylene)amino)-5-phenylpent-4-enoate + (2R,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-53-3) + (2R,3R)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester + (2S,3S)-2-(benzhydrylidenylamino)-3-phenylpent-4-enoic acid tert-butyl ester (586418-52-2)

Guidance literature:

(E)-cinnamyl diethyl phosphate; With chiral bidentate phosphite-type ligand; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

N-(diphenylmethylene)glycine tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo034638f

upstream raw materials:

cinnamyl benzoate

N-(diphenylmethylene)glycine tert-butyl ester

(E)-cinnamyl diethyl phosphate

1-phenyl-2-propenyl acetate

Downstream raw materials:

(2S,3S)-2-tert-butoxycarbonylamino-3-phenylpent-4-enoic acid tert-butyl ester