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

Base Information

Chemical Name:6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine
CAS No.:945034-03-7
Molecular Formula:C₄₁H₅₇N₇O₁₄S
Molecular Weight:904.008
Hs Code.:

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

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

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

There total 4 articles about 6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine 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: 66.0%

: 945034-01-5
6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylideneadenosine

: 945034-03-7
6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine

Guidance literature:: With sulphamoyl chloride; In N,N-dimethyl acetamide; at 0 - 20 ℃; for 2h;
DOI:10.1021/ja0721521

Reference yield:

: 139301-93-2
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

: 945034-03-7
6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine

Guidance literature:: Multi-step reaction with 6 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: 56 percent / Grubbs II ruthenium catalyst / CH₂Cl₂ / 24 h / Heating

5.1: 89 percent / HF*pyridine / tetrahydrofuran / 1.17 h / 20 °C

6.1: 66 percent / sulfamoyl chloride / N,N-dimethyl-acetamide / 2 h / 0 - 20 °C

With dmap; n-butyllithium; sulphamoyl chloride; 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; N,N-dimethyl acetamide;
DOI:10.1021/ja0721521

Reference yield:

: 945033-96-5
5'-O-t-butyldimethylsilyl-8-iodo-2',3'-O-isopropylideneadenosine

: 945034-03-7
6-N-bis(t-butoxycarbonyl)-8-(O-benzyl-N-[t-butoxycarbonyl]-L-2''-E/Z-crotylglycin-6''-yl)-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine

Guidance literature:: Multi-step reaction with 5 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: 56 percent / Grubbs II ruthenium catalyst / CH₂Cl₂ / 24 h / Heating

4: 89 percent / HF*pyridine / tetrahydrofuran / 1.17 h / 20 °C

5: 66 percent / sulfamoyl chloride / N,N-dimethyl-acetamide / 2 h / 0 - 20 °C

With dmap; sulphamoyl chloride; 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; N,N-dimethyl acetamide;
DOI:10.1021/ja0721521