2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

Base Information

Chemical Name:2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine
CAS No.:860651-69-0
Molecular Formula:C₃₆H₄₀N₂O₇Si
Molecular Weight:640.808
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

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Technology Process of 2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

There total 4 articles about 2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine 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: 51.0%

: 860651-66-7
1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-vinyl-α,β-D-ribofuranose

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 860651-69-0
2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 1h; Heating;
DOI:10.1055/s-2005-865328

Reference yield:

: 454715-81-2
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-vinyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

: 860651-69-0
2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / AcOH; H₂SO₄ / 16 h / 20 °C

2: 51 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; In acetonitrile;
DOI:10.1055/s-2005-865328

Reference yield:

: 212970-72-4
{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

: 860651-69-0
2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-vinyluridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

2.2: 97 percent / hexane; tetrahydrofuran / 3.5 h / -78 - 20 °C

3.1: 90 percent / AcOH; H₂SO₄ / 16 h / 20 °C

4.1: 51 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

With n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; Dess-Martin periodane; acetic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 2.2: Wittig reaction;
DOI:10.1055/s-2005-865328