(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester
CAS No.:213454-19-4
Molecular Formula:C₂₀H₂₃BrN₂O₈
Molecular Weight:499.315
Hs Code.:

Synonyms:(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

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Chemical Property of (E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

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Technology Process of (E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

There total 14 articles about (E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl 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:

: 213454-18-3
methyl (2E,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

: 213454-19-4
(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

Guidance literature:: With triethylsilane; palladium diacetate;
DOI:10.1021/jo981006y

Reference yield:

: (S)-2-{(1R,2S)-2-Acetoxy-3-bromo-4-methoxycarbonyl-4-[(E)-methoxycarbonylimino]-1-phenylacetoxy-butyl}-aziridine-1-carboxylic acid benzyl ester

: 213454-19-4
(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: base

2: Et₃SiH; Pd(OAc)2

With triethylsilane; palladium diacetate; 1: tautomerization / 2: decarbobenzoxylation;
DOI:10.1021/ja992274w

Reference yield:

: 103-82-2
phenylacetic acid

: 213454-19-4
(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: DDC; DMAP

2.1: HF

3.1: Et₃N

4.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

5.1: O₃

5.2: (CH₃)2S

6.1: LiCl; i-Pr₂NEt / acetonitrile

7.1: N-bromosuccinimide / CHCl₃ / 40 °C

8.1: base

9.1: Et₃SiH; Pd(OAc)2

With triethylsilane; dmap; palladium diacetate; N-Bromosuccinimide; hydrogen fluoride; potassium tert-butylate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; lithium chloride; In tetrahydrofuran; chloroform; acetonitrile; 1.1: Esterification / 2.1: desilylation / 3.1: Acetylation / 4.1: Cyclization / 5.1: ozonization / 5.2: Reduction / 6.1: olefination / 7.1: Bromination / 8.1: tautomerization / 9.1: decarbobenzoxylation;
DOI:10.1021/ja992274w