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

Base Information

• Chemical Name: 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
• CAS No.: 916595-33-0
• Molecular Formula: C₃₉H₄₄Br₂N₆O₉
• Molecular Weight: 900.621
• Mol file: 916595-33-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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:

ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate (916154-87-5) → 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 (916595-33-0)

Guidance literature:

With pyridinium hydrobromide perbromide; In 1,4-dioxane; at 20 ℃; for 8h;

DOI:10.1021/ol062026m

Reference yield:

ethyl 2-N-(diphenylmethyleneamino)hex-5-enoate (912651-56-0) → 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 (916595-33-0)

Guidance literature:

Multi-step reaction with 4 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

4: pyridinium tribromide / dioxane / 8 h / 20 °C

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

DOI:10.1021/ol062026m

Reference yield:

6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine (916154-77-3) → 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 (916595-33-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: pyridinium tribromide / dioxane / 8 h / 20 °C

With Hoveyda-Grubbs catalyst second generation; pyridinium hydrobromide perbromide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ol062026m

upstream raw materials:

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

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

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

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