methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate

Base Information

• Chemical Name: methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate
• CAS No.: 213454-20-7
• Molecular Formula: C₂₀H₂₂N₂O₈
• Molecular Weight: 418.403

Synonyms:methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate

Chemical Property of methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate

Chemical Property:

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Technology Process of methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate

There total 15 articles about methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ^2α-acetate 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: 52.0%

(E)-(4S,5R)-4-Acetoxy-5-(S)-aziridin-2-yl-3-bromo-2-methoxycarbonylamino-5-phenylacetoxy-pent-2-enoic acid methyl ester (213454-19-4) → methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ2α-acetate (213454-20-7)

Guidance literature:

With Dowex 1X₈-400 (carbonate form); In chloroform; at 35 ℃; for 18h;

DOI:10.1007/BF02317807

Reference yield:

(S)-2-{(1R,2S)-2-Acetoxy-3-bromo-4-methoxycarbonyl-4-[(E)-methoxycarbonylimino]-1-phenylacetoxy-butyl}-aziridine-1-carboxylic acid benzyl ester → methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ2α-acetate (213454-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: base

2: Et₃SiH; Pd(OAc)2

3: 52 percent / N-methylmorpholine

With 4-methyl-morpholine; triethylsilane; palladium diacetate; 1: tautomerization / 2: decarbobenzoxylation / 3: Cyclization;

DOI:10.1021/ja992274w

Reference yield:

phenylacetic acid (103-82-2) → methyl (2E,3R,4R,5S)-3-acetoxy-α-methoxycarbonylamino-4-phenylacetoxy-1-azabicyclo[3.1.0]-hexene-Δ2α-acetate (213454-20-7)

Guidance literature:

Multi-step reaction with 10 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

10.1: 52 percent / N-methylmorpholine

With 4-methyl-morpholine; 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 / 10.1: Cyclization;

DOI:10.1021/ja992274w

upstream raw materials:

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

phenylacetic acid

(S)-2-((1R,2S)-2-Acetoxy-3-oxo-1-phenylacetoxy-propyl)-aziridine-1-carboxylic acid benzyl ester

[(E)-(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-hex-4-enyl]-carbamic acid benzyl ester

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