tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Base Information

Chemical Name:tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate
CAS No.:461696-67-3
Molecular Formula:C₂₃H₃₃NO₆
Molecular Weight:419.518
Hs Code.:

Synonyms:tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

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Chemical Property of tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Chemical Property:

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Technology Process of tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

There total 3 articles about tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate 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:

: (ethoxy-methoxymethyl-phosphinoyl)-acetic acid tert-butyl ester

: Acetic acid (1S,2R)-2-tert-butoxycarbonylamino-1-formyl-3-phenyl-propyl ester

: 461696-67-3
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 ℃; for 4.33h;
DOI:10.1021/jo025923m

Reference yield:

: 139397-08-3
(3R,4R)-4-(tert-Butoxycarbonylamino)-5-phenylpent-1-en-3-ol

: 461696-67-3
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / 4-(dimethylamino)pyridine; pyridine / CHCl₃ / 3 h / 0 - 20 °C

2.1: O₃ / ethyl acetate / -78 °C

2.2: Me₂S / ethyl acetate / 0.5 h / 0 °C

3.1: 5.38 g / LiCl; (i-Pr)2NEt / acetonitrile / 4.33 h / 0 °C

With pyridine; dmap; ozone; N-ethyl-N,N-diisopropylamine; lithium chloride; In chloroform; ethyl acetate; acetonitrile; 3.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo025923m

Reference yield:

: 461696-66-2
(3R,4R)-O-acetyl-4-[N-(tert-butoxycarbonyl)amino]-5-phenylpent-1-en-3-ol

: 461696-67-3
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / ethyl acetate / -78 °C

1.2: Me₂S / ethyl acetate / 0.5 h / 0 °C

2.1: 5.38 g / LiCl; (i-Pr)2NEt / acetonitrile / 4.33 h / 0 °C

With ozone; N-ethyl-N,N-diisopropylamine; lithium chloride; In ethyl acetate; acetonitrile; 2.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo025923m