Adenosine, N-benzoyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4-methoxyphenyl)diphenylmethyl]-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Base Information

• Chemical Name: Adenosine, N-benzoyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4-methoxyphenyl)diphenylmethyl]-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]
• CAS No.: 135711-69-2
• Molecular Formula: C₅₂H₆₄N₇O₇PSi
• Molecular Weight: 958.182
• DSSTox Substance ID: DTXSID301100117
• Mol file: 135711-69-2.mol

Synonyms:DTXSID301100117;135711-69-2

Chemical Property of Adenosine, N-benzoyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4-methoxyphenyl)diphenylmethyl]-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 21
• Exact Mass: 957.43741094
• Heavy Atom Count: 68
• Complexity: 1580

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=CC=C6)C7=CC=C(C=C7)OC
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@@H]1[C@H](O[C@H]([C@@H]1O[Si](C)(C)C(C)(C)C)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=CC=C6)C7=CC=C(C=C7)OC

Technology Process of Adenosine, N-benzoyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4-methoxyphenyl)diphenylmethyl]-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

There total 1 articles about Adenosine, N-benzoyl-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4-methoxyphenyl)diphenylmethyl]-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite] 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%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine (69504-09-2) → N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine 3'-(2-Cyanoethyl N,N-Diisopropylphosphoroamidite) (135711-69-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/hlca.19910740420

Reference yield:

N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine 3'-(2-Cyanoethyl N,N-Diisopropylphosphoroamidite) (135711-69-2) + (PS)-N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-(OP-(2-cyanoethyl)>->5')-N6-benzoyl-2',3'-bis-O-<(tert-butyl)dimethylsilyl>adenosine (135711-74-9) → (PR)-N6-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PS)-N6-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N6-benzoyl-2',3'-bis-O-..... (135711-72-7,135818-65-4,135818-66-5,135818-67-6) + (PS)-N6-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PS)-N6-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N6-benzoyl-2',3'-bis-O-..... (135711-72-7,135818-65-4,135818-66-5,135818-67-6)

Guidance literature:

With sulfur; 3-nitro-1,2,4-triazole; Yield given. Multistep reaction. Yields of byproduct given; 1) MeCN, r.t., 2 h, 2) pyridine, 20 h;

DOI:10.1002/hlca.19910740420

Reference yield:

N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine 3'-(2-Cyanoethyl N,N-Diisopropylphosphoroamidite) (135711-69-2) + (PR)-N6-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-N6-benzoyl-2',3'-bis-O-<(tert-butyl)dimethylsilyl>adenosine (135711-74-9) → (PR)-N6-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PR)-N6-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N6-benzoyl-2',3'-bis-O-..... (135711-72-7,135818-65-4,135818-66-5,135818-67-6) + (PS)-N6-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PR)-N6-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N6-benzoyl-2',3'-bis-O-..... (135711-72-7,135818-65-4,135818-66-5,135818-67-6)

Guidance literature:

With sulfur; 3-nitro-1,2,4-triazole; Yield given. Multistep reaction. Yields of byproduct given; 1) MeCN, r.t., 2 h, 2) pyridine, 20 h;

DOI:10.1002/hlca.19910740420

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N⁶-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine

Downstream raw materials:

(PR)-N⁶-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-P-thioadenylyl-(3-P-(2-cyanoethyl)>->5')-N⁶-benzoyl-2',3'-bis-O-<(tert-butyl)dimethylsilyl>adenosine

(PS)-N⁶-Benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-P-thioadenylyl-(3-<(O^P-(2-cyanoethyl)>->5')-N⁶-benzoyl-2',3'-bis-O-<(tert-butyl)dimethylsilyl>adenosine

(PR)-N⁶-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PS)-N⁶-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N⁶-benzoyl-2',3'-bis-O-.....

(PS)-N⁶-Benzoyl-2'--5'-O-(monomethoxytrityl)-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5')-(PS)-N⁶-benzoyl-2'-O-<(tert-butyl)dimethylsilyl>-P-thioadenylyl-(3'-P-(2-cyanoethyl)>->5)-N⁶-benzoyl-2',3'-bis-O-.....