ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Base Information

• Chemical Name: ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate
• CAS No.: 916154-87-5
• Molecular Formula: C₃₉H₄₄N₆O₉
• Molecular Weight: 740.813
• Mol file: 916154-87-5.mol

Synonyms:ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Chemical Property of ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

There total 6 articles about ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate 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: 76.0%

6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine (916154-77-3) + (RS)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate (756498-97-2) → ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate (916154-87-5)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 65 ℃;

DOI:10.1021/ol062026m

Reference yield:

ethyl 2-N-(diphenylmethyleneamino)hex-5-enoate (912651-56-0) → ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate (916154-87-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. HCl / diethyl ether / 0 - 20 °C

2: 79 percent / NaHCO₃ / dioxane; H₂O / 18 h / 20 °C

3: 76 percent / 1,3-(bis-mesityl-2-imidazolidinylidene)(o-iPrO-PhCH=)RuCl₂ / CH₂Cl₂ / 65 °C

With hydrogenchloride; Hoveyda-Grubbs catalyst second generation; sodium hydrogencarbonate; In 1,4-dioxane; diethyl ether; dichloromethane; water;

DOI:10.1021/ol062026m

Reference yield:

5'-deoxy-2',3'-O-isopropylidene-5'-methyleneadenosine (65969-38-2) → ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate (916154-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 0 - 20 °C

2: 76 percent / 1,3-(bis-mesityl-2-imidazolidinylidene)(o-iPrO-PhCH=)RuCl₂ / CH₂Cl₂ / 65 °C

With pyridine; Hoveyda-Grubbs catalyst second generation; In dichloromethane;

DOI:10.1021/ol062026m

upstream raw materials:

6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine

(RS)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate

ethyl 2-N-(diphenylmethyleneamino)hex-5-enoate

5'-deoxy-2',3'-O-isopropylidene-5'-methyleneadenosine

Downstream raw materials:

5,6-Dibromo-2-tert-butoxycarbonylamino-6-[(3aS,4S,6R,6aR)-6-(6-dibenzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hexanoic acid ethyl ester