5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

Base Information

Chemical Name:5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester
CAS No.:292054-00-3
Molecular Formula:C₅₃H₇₈N₆O₁₀Si₃
Molecular Weight:1043.49
Hs Code.:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

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Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

There total 9 articles about 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl 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: 45.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 292053-99-7
5'-O-(4,4'-dimethoxytrityl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

: 292054-00-3
5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

: 292053-98-6
5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

Guidance literature:: With pyridine; for 24h;
DOI:10.1021/jo000338b

Reference yield:

: 33422-70-7
ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate

: 292054-00-3
5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / pyridine

2: 95 percent / Et₃N / CH₂Cl₂ / 4 h

3: 95 percent / NH₃ / methanol / 0.02 h

4: 91 percent / DCC; pyridine / 0.08 h / 20 °C

5: 95 percent / NH₃ / methanol / 6 h / 20 °C

6: 95 percent / pyridine / 5 h / 20 °C

7: pyridine / 24 h

With pyridine; ammonia; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: Condensation / 2: Condensation / 3: ester cleavage / 4: Esterification / 5: ester cleavage / 6: Condensation / 7: Condensation;
DOI:10.1021/jo000338b

Reference yield:

: 7387-57-7,953089-09-3
triacetyladenosine

: 292054-00-3
5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / pyridine

2: 90 percent / pyridine

3: 95 percent / Et₃N / CH₂Cl₂ / 4 h

4: 95 percent / NH₃ / methanol / 0.02 h

5: 91 percent / DCC; pyridine / 0.08 h / 20 °C

6: 95 percent / NH₃ / methanol / 6 h / 20 °C

7: 95 percent / pyridine / 5 h / 20 °C

8: pyridine / 24 h

With pyridine; ammonia; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: Condensation / 2: Condensation / 3: Condensation / 4: ester cleavage / 5: Esterification / 6: ester cleavage / 7: Condensation / 8: Condensation;
DOI:10.1021/jo000338b