5'-O-tert-butyldiphenylsilylthymidine

Base Information

• Chemical Name: 5'-O-tert-butyldiphenylsilylthymidine
• CAS No.: 101527-40-6
• Molecular Formula: C₂₆H₃₂N₂O₅Si
• Molecular Weight: 480.636
• Mol file: 101527-40-6.mol

Synonyms:5'-O-tert-butyldiphenylsilylthymidine

Chemical Property of 5'-O-tert-butyldiphenylsilylthymidine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

5'-O-tert-Butyldiphenylsilyl-thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-tert-butyldiphenylsilylthymidine

There total 23 articles about 5'-O-tert-butyldiphenylsilylthymidine 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-O-tert-butyldiphenylsilylthymidine (101527-40-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at -50 - 20 ℃; for 4h;

DOI:10.3390/molecules23061457

Reference yield: 78.0%

5'-O-(tert-butyldiphenylsilyl)-3'-keto-2'-deoxythymidine (305819-88-9) → 5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) + 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine (166955-29-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1002/jccs.200100139

Reference yield:

(2R,3S,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-((4-ethynylbenzyl)(piperidin-2-ylmethyl)amino)ethyl) carbonate → C17H22N2 + 5'-O-tert-butyldiphenylsilylthymidine (101527-40-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 90 ℃; Temperature; Solvent;

upstream raw materials:

1-[4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

tert-butylchlorodiphenylsilane

thymidine

3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine

Downstream raw materials:

1-<5-O-(tert-butyldiphenylsilyl)-3-O-<(phenoxy)thiocarbonyl>-2-deoxy-β-D-erythro-pentofuranosyl>thymine

4-Methyl-benzoic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

carbonic acid 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester

1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(pentafluorophenoxy)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine

Refernces

• 1、 Ding, Yili,Deng, Rilie,Wang, Bingyun. "Synthesis of 2-deoxy ribose related disaccharide nucleoside and its phosphoramidite". . p. 3848 - 3852. Retrieved 2017.
• 2、 Rejman, Dominik,Kralikova, Sarka,Tocik, Zdenek,Liboska, Radek,Rosenberg, Ivan. "Selective cleavage of O-(dimethoxytrityl) protecting group with sodium periodate". . p. 502 - 508. Retrieved 2002.
• 3、 -. "MODIFIED NUCLEOTIDES AND USES THEREOF". Paragraph 0401-0402; 0406. . Retrieved 2021/10/30.
• 4、 -. "NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS". Paragraph 0313; 0317. . Retrieved 2019/11/04.