6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine
• CAS No.: 945034-02-6
• Molecular Formula: C₄₁H₅₆N₆O₁₂
• Molecular Weight: 824.929
• Mol file: 945034-02-6.mol

Synonyms:6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine

Chemical Property of 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine

There total 3 articles about 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine 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: 86.0%

6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-5'-O-t-butyldimethylsilyl-2',3'-O-isopropylideneadenosine (945034-00-4) → 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine (945034-02-6)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1.16667h;

DOI:10.1021/ja0721521

Reference yield:

9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (139301-93-2) → 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine (945034-02-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 84 percent / I₂ / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.1: 95 percent / Pd(PPh₃)4 / hexamethylphosphoric acid triamide / 1 h / 90 °C

3.1: 72 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 18 h / 0 - 20 °C

4.1: 46 percent / Grubbs II ruthenium catalyst / CH₂Cl₂ / 24 h / Heating

5.1: 86 percent / HF*pyridine / tetrahydrofuran / 1.17 h / 20 °C

With dmap; n-butyllithium; pyridine hydrogenfluoride; diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;

DOI:10.1021/ja0721521

Reference yield:

5'-O-t-butyldimethylsilyl-8-iodo-2',3'-O-isopropylideneadenosine (945033-96-5) → 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine (945034-02-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Pd(PPh₃)4 / hexamethylphosphoric acid triamide / 1 h / 90 °C

2: 72 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 18 h / 0 - 20 °C

3: 46 percent / Grubbs II ruthenium catalyst / CH₂Cl₂ / 24 h / Heating

4: 86 percent / HF*pyridine / tetrahydrofuran / 1.17 h / 20 °C

With dmap; pyridine hydrogenfluoride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/ja0721521

upstream raw materials:

6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-5'-O-t-butyldimethylsilyl-2',3'-O-isopropylideneadenosine

5'-O-t-butyldimethylsilyl-8-iodo-2',3'-O-isopropylideneadenosine

9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

Downstream raw materials:

6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-DL-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine