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

Base Information

Chemical Name: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
CAS No.:945034-00-4
Molecular Formula:C₄₇H₇₀N₆O₁₂Si
Molecular Weight:939.191
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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: 46.0%

: 945033-98-7
8-allyl-6-N-bis(t-butoxycarbonyl)-5'-O-t-butyldimethylsilyl-2',3'-O-isopropylideneadenosine

: 124097-05-8
O-benzyl-N-t-butoxycarbonyl-DL-2-allylglycine

: 945034-00-4
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

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 24h; Heating;
DOI:10.1021/ja0721521

Reference yield:

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

Guidance literature:: Multi-step reaction with 3 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

With dmap; 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

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

: 945034-00-4
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

Guidance literature:: Multi-step reaction with 4 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

With dmap; n-butyllithium; 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