1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

Base Information

Chemical Name:1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine
CAS No.:151989-81-0
Molecular Formula:C₂₇H₃₂N₂O₄Si
Molecular Weight:476.648
Hs Code.:

Synonyms:1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

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Chemical Property of 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

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Technology Process of 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

There total 8 articles about 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine 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: 80.0%

: 151989-78-5
1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methanesulfonyl-4-C-methyl-β-D-threo-pentofuranosyl)thymine

: 151989-81-0
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 70 ℃; for 24h;
DOI:10.1135/cccc19931668

Reference yield:

: 151767-33-8
1-(2-deoxy-4-C-hydroxymethyl-α-L-erythro-pentofuranosyl)thymine

: 151989-81-0
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / H₂SO₄ / acetone / 0.33 h / Ambient temperature

2: 84 percent / hexamethylphosphoric triamide, thionyl chloride / Ambient temperature

3: 81 percent / tributylstannane, 2,2'-azobis(2-methylpropionitrile) / toluene / 0.67 h / 100 °C

4: 86 percent / dowex 50 (H⁺ form) / methanol; H₂O / 2 h / Heating

5: 88 percent / imidazole / dimethylformamide / Ambient temperature

6: 83 percent / pyridine / 5 h / Ambient temperature

7: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 24 h / 70 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; 2,2'-azobis(isobutyronitrile); Dowex 50 (H⁺ form); sulfuric acid; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1135/cccc19931668

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 151989-81-0
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / imidazole / dimethylformamide / Ambient temperature

2: 83 percent / pyridine / 5 h / Ambient temperature

3: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 24 h / 70 °C

With 1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1135/cccc19931668