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

Base Information

Chemical Name:tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate
CAS No.:461696-74-2
Molecular Formula:C₂₄H₃₅NO₆
Molecular Weight:433.545
Hs Code.:

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

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Chemical Property of tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate

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Technology Process of tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate

There total 18 articles about tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-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: 93.0%

: 108-24-7
acetic anhydride

: 420837-88-3
tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-3-methyl-6-phenylhex-2-enoate

: 461696-74-2
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate

Guidance literature:: With pyridine; dmap; In chloroform;
DOI:10.1021/ol016834j

Reference yield:

: 106454-69-7
N-tert-butoxycarbonyl-D-Phenylalaninol

: 461696-74-2
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO; (i-Pr)2NEt / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: 30.2 g / tetrahydrofuran / 3 h / -78 - 0 °C

3.1: (COCl)2; DMSO; (i-Pr)2NEt / CH₂Cl₂ / 1.25 h / -78 - 0 °C

4.1: 4.59 g / Zn(BH₄)2 / diethyl ether / 1 h / -78 - 0 °C

5.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / CHCl₃ / 3 h / 0 - 20 °C

6.1: O₃ / ethyl acetate / -78 °C

6.2: Me₂S / ethyl acetate / 0 °C

7.1: 4.29 g / CHCl₃ / 48 h / Heating

8.1: Na₂CO₃ / methanol / 3 h / 20 °C

9.1: 93 percent / 4-dimethylaminopyridine; pyridine

With pyridine; dmap; zinc(II) tetrahydroborate; oxalyl dichloride; sodium carbonate; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; 1.1: Swern oxidation / 3.1: Swern oxidation / 7.1: Wittig reaction;
DOI:10.1021/jo025923m

Reference yield:

: 482374-27-6
(1-benzyl-2-hydroxy-3-methyl-but-3-enyl)-carbamic acid tert-butyl ester

: 461696-74-2
tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)amino]-3-methyl-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: (COCl)2; DMSO; (i-Pr)2NEt / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: 4.59 g / Zn(BH₄)2 / diethyl ether / 1 h / -78 - 0 °C

3.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / CHCl₃ / 3 h / 0 - 20 °C

4.1: O₃ / ethyl acetate / -78 °C

4.2: Me₂S / ethyl acetate / 0 °C

5.1: 4.29 g / CHCl₃ / 48 h / Heating

6.1: Na₂CO₃ / methanol / 3 h / 20 °C

7.1: 93 percent / 4-dimethylaminopyridine; pyridine

With pyridine; dmap; zinc(II) tetrahydroborate; oxalyl dichloride; sodium carbonate; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; 1.1: Swern oxidation / 5.1: Wittig reaction;
DOI:10.1021/jo025923m