1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

Base Information

Chemical Name:1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine
CAS No.:230631-34-2
Molecular Formula:C₃₉H₄₀N₂O₁₁S₂
Molecular Weight:776.885
Hs Code.:

Synonyms:1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

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Chemical Property of 1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

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Technology Process of 1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

There total 8 articles about 1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]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: 71.0%

: 98-59-9
p-toluenesulfonyl chloride

: 230631-33-1
1-(3,5-Di-O-benzyl-β-D-allofuranosyl)thymine

: 230631-34-2
1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1039/a901729a

Reference yield: 71.0%

: 1122-58-3
dmap

: 98-59-9
p-toluenesulfonyl chloride

: 230631-33-1
1-(3,5-Di-O-benzyl-β-D-allofuranosyl)thymine

: 230631-34-2
1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

Guidance literature:: In methanol; dichloromethane; water;

Reference yield:

: 100-39-0
benzyl bromide

: 230631-34-2
1-[3,5-Di-O-benzyl-2,6-di-O-(p-tolylsulfonyl)-β-D-allofuranosyl]thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.5 h

1.2: 90 percent / dimethylformamide / 2 h / 20 °C

2.1: AcOH / 10 h / 80 °C

3.1: pyridine / CH₂Cl₂ / 20 h / 20 °C

4.1: 81 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 2 h / Heating

5.1: 88 percent / NaOCH₃ / methanol / 14 h / 20 °C

6.1: 71 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Acetolysis / 3.1: Acetylation / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Tosylation;
DOI:10.1039/a901729a