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

Base Information

Chemical Name:methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate
CAS No.:213454-22-9
Molecular Formula:C₂₈H₂₉BrN₂O₁₀
Molecular Weight:633.45
Hs Code.:

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

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Chemical Property of methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

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Technology Process of methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

There total 14 articles about methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate 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:

: 117833-92-8
(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

: 213454-22-9
methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: MgBr₂*Et₂O / -20 °C

1.2: 95 percent / CH₂Cl₂ / 25 °C

2.1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

3.1: Et₃N

4.1: DDC; DMAP

5.1: HF

6.1: Et₃N

7.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

8.1: O₃

8.2: (CH₃)2S

9.1: LiCl; i-Pr₂NEt / acetonitrile

10.1: N-bromosuccinimide / CHCl₃ / 40 °C

11.1: base

With dmap; N-Bromosuccinimide; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ozone; ethylene glycol; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; lithium chloride; magnesium bromide; In tetrahydrofuran; chloroform; acetonitrile; 1.1: complexation / 1.2: Addition / 2.1: Ring cleavage / 3.1: mesylation / 4.1: Esterification / 5.1: desilylation / 6.1: Acetylation / 7.1: Cyclization / 8.1: ozonization / 8.2: Reduction / 9.1: olefination / 10.1: Bromination / 11.1: tautomerization;
DOI:10.1021/ja992274w

Reference yield:

: 213454-17-2
(S)-2-((Z)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

: 213454-22-9
methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

Guidance literature:: Multi-step reaction with 2 steps

1: N-bromosuccinimide / CHCl₃ / 40 °C

2: base

With N-Bromosuccinimide; In chloroform; 1: Bromination / 2: tautomerization;
DOI:10.1021/ja992274w

Reference yield:

: 103-82-2
phenylacetic acid

: 213454-22-9
methyl (2Z,4S,5R)-4-acetoxy-5-[(2S)-N-(benzyloxycarbonyl)aziridin-2-yl]-3-bromo-5-phenylacetoxy-2-[N-methoxycarbonylamino]-2-pentenoate

Guidance literature:: Multi-step reaction with 8 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

With dmap; 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;
DOI:10.1021/ja992274w