{(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester
• CAS No.: 873017-34-6
• Molecular Formula: C₃₄H₅₅N₅O₇
• Molecular Weight: 645.84

Synonyms:

Chemical Property of {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester

There total 17 articles about {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl 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:

(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester (92136-57-7) → {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester (873017-34-6)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. Cs₂CO₃

2: EDCI; HOBT; TEA / DMAP

3: aq. Cs₂CO₃

4: EDCI; HOBT; TEA / DMAP

5: bis(tricyclohexylphosphine)benzylideneruthenium dichloride

6: 100 percent / H₂

7: 2-hydroxypyridine / Heating

With 2-hydroxypyridin; Grubbs catalyst first generation; TEA; hydrogen; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; 5: Grubbs cyclization;

DOI:10.1016/j.bmcl.2005.09.003

Reference yield:

(S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid (208522-13-8) → {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester (873017-34-6)

Guidance literature:

Multi-step reaction with 6 steps

1: EDCI; HOBT; TEA / DMAP

2: aq. Cs₂CO₃

3: EDCI; HOBT; TEA / DMAP

4: bis(tricyclohexylphosphine)benzylideneruthenium dichloride

5: 100 percent / H₂

6: 2-hydroxypyridine / Heating

With 2-hydroxypyridin; Grubbs catalyst first generation; TEA; hydrogen; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; 4: Grubbs cyclization;

DOI:10.1016/j.bmcl.2005.09.003

Reference yield:

(S)-2-[N(2)-[(tert-butyloxy)carbonyl]amino]-N-methoxyl-N-methyl-5-hexenoic amide (208522-14-9) → {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester (873017-34-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LiAlH₄

2.1: Zn-Cu; Ti(IV) / N,N-dimethyl-acetamide

2.2: N,N-dimethyl-acetamide

3.1: acetic acid / 110 °C

4.1: LHMDS

5.1: EDCI; HOBT; TEA / DMAP

6.1: bis(tricyclohexylphosphine)benzylideneruthenium dichloride

7.1: 100 percent / H₂

8.1: 2-hydroxypyridine / Heating

With 2-hydroxypyridin; titanium; lithium aluminium tetrahydride; Grubbs catalyst first generation; TEA; hydrogen; copper; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; zinc; dmap; In N,N-dimethyl acetamide; 6.1: Grubbs cyclization;

DOI:10.1016/j.bmcl.2005.09.003

upstream raw materials:

[(3S,6S,13S)-3-Methyl-13-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-2,5-dioxo-1,4-diaza-cyclotridec-6-yl]-carbamic acid tert-butyl ester

L-valine benzylamide

(S)-5-((S)-1-Amino-pent-4-enyl)-dihydro-furan-2-one

(3R,5S)-5-((S)-1-Amino-pent-4-enyl)-3-methyl-dihydro-furan-2-one

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